4 Conclusions
• Male bumble bee labial glands (LGs) contain various fatty alcohols. In Bombus lapidarius, these are both saturated and unsaturated C16. InB. terrestrisandB. lucorum, the fatty alco- hols range from short chains (C14) to very long chains (up to C26). Male LGs of the latter two species also contain unsaturated fatty alcohols, e.g. 9Z12Z15Z-18: or 15Z-20:. In general, the LG fatty alcohols partially correspond to specificities determined for abundantly expressed FARs, i.e. for FAR-A4 and FAR-A5 fromB. lapidarius, and for FAR-A1 and FAR-A2s fromB.
terrestrisandB. lucorum. All of these LG-specific FARs belong to a single orthologous group – the FAR-A. Phylogenetic analysis indicates an expansion of FAR-A group only among the species from bumble bee (Bombini) and stingless bee (Meliponini) clades. Notably, transpos- able elements have been specifically detected in the vicinity of FAR-A genes in two bumble bee genomes. The TE-mediated duplications thus might play an important role in FAR evolution in Hymenoptera.
• The effects of introducing identical residues at position 224 in desaturases D2 and D3 from Manduca sextaon their specificity are similar. The switching mechanism between Δ11/conjugase specificity observed in wild type D2, and Δ14specificity observed in D3 are most likely gov- erned by residue bulkiness and hydrophobic effect. With smaller and more hydrophilic residues, alanine and threonine, both D2 and D3 perform Δ11desaturation and 1,4-conjugation on 16:
and 11Z-16: substrates, respectively. Upon introduction of larger and more hydrophobic residues, valine and isoleucine, the specificity shifts in both enzymes towards Δ14desatura- tion of 10E12E-16: substrate. Interestingly, in Δ11desaturase/conjugase D1 from evolution- airly more distant lepidopteran, Bombyx mori, the tunnel bend residue-derived specificity switching from Δ11/conjugase (with threonine residue) to Δ14(with isoleucine residue) is also conserved.
• Disruption of a proton transfer chain (PTC) in soluble Δ9desaturase fromRicinus communis by introducing homologous residues from methane monooxygenase, which has structurally similar active site architecture, leads to increased substrate hydroxylation. Furthermore, aside from alcohols, the mutations promote formation of other oxygenated products, e.g. allylic alcohols, epoxides and diols. The desaturase accepts not only saturated and monounsaturated fatty acyls as substrates, but also monohydroxylated fatty acyls. The effect of PTC disruption can be explained by a limited access of protons to the active site which are necessary for water release during desaturation reaction.
References
[1] Mahadevan, V.Prog. Chem. Fats Other Lipids,15(4):255–299, 1977. DOI:10.1016/0079-6832(77)90010-6. [2] Sand, D. M., Hehl, J. L., and Schlenk, H. Biochemistry,8(12):4851–4854, 1969. DOI:10.1021/bi00840a030.
[3] Lee, T.J. Biol. Chem.,254(8):2892–2896, 1979. DOI:10.1016/S0021-9258(17)30157-6.
[4] Morse, D. and Meighen, E. A.J. Chem. Ecol.,16(5):1485–1493, 1990. DOI:10.1007/BF01014083.
[5] Luxová, A. and Svatoš, A. J. Mol. Catal. B Enzym.,38(1):37–42, 2006. DOI:10.1016/j.molcatb.2005.10.006.
[6] Day, J. I. E., Goldfine, H., and Hagen, P.-O. Biochim. Biophys. Acta Lipids Lipid Metabol.,218(1):179–182, 1970. DOI:
10.1016/0005-2760(70)90108-6.
[7] Kolattukudy, P. E.Arch. Biochem. Biophys.,142(2):701–709, 1971. DOI:10.1016/0003-9861(71)90536-4.
[8] Khan, A. A. and Kolattukudy, P. E.Arch. Biochem. Biophys.,170:400–408, 1975. DOI:10.1016/0003-9861(75)90135-6. [9] Rock, C. O., Fitzgerald, V., and Snyder, F.Arch. Biochem. Biophys.,186(1):77–83, 1978. DOI:10.1016/0003-9861(78)90465-4. [10] Wykle, M. L., Malone, B., and Snyder, F. J. Lipid Res.,20(7):890–896, 1979. DOI:10.1016/S0022-2275(20)40018-5. [11] Bishop, J. E. and Hajra, A. K. J. Biol. Chem.,256(18):9542–9550, 1981. DOI:10.1016/S0021-9258(19)68796-X. [12] Moore, C. and Snyder, F. Arch. Biochem. Biophys.,214(2):489–499, 1982. DOI:10.1016/0003-9861(82)90052-2. [13] Ozawa, R. and Matsumoto, S. Insect Biochem. Mol. Biol.,26(3):259–265, 1996. DOI:10.1016/0965-1748(95)00088-7. [14] Riendeau, D. and Meighen, E. Experientia,41(6):707–713, 1985. DOI:10.1007/BF02012564.
[15] Wang, X. and Kolattukudy, P. E. FEBS Lett.,370(1-2):15–18, 1995. DOI:10.1016/0014-5793(95)00781-4. [16] Vioque, J. and Kolattukudy, P. E. Arch. Biochem. Biophys.,340(1):64–72, 1997. DOI:10.1006/abbi.1997.9932.
[17] Metz, J. G., Pollard, M. R., Anderson, L., Hayes, T. R., and Lassner, M. W. Plant Physiol.,122(3):635–644, 2000. DOI:
10.1104/pp.122.3.635.
[18] Kavanagh, K. L., Jörnvall, H., Persson, B., and Oppermann, U. Cell. Mol. Life Sci., 65(24):3895–3906, 2008. DOI:
10.1007/s00018-008-8588-y.
[19] Persson, B., Kallberg, Y., Bray, J. E., Bruford, E., Dellaporta, S. L., Favia, A. D., Duarte, R. G., Jörnvall, H., Kavanagh, K. L., Kedishvili, N., Kisiela, M., Maser, E., Mindnich, R., Orchard, S., Penning, T. M., Thornton, J. M., Adamski, J., and Oppermann, U. Chem.-Biol. Interact.,178(1-3):94–98, 2009. DOI:10.1016/j.cbi.2008.10.040.
[20] Kolattukudy, P. E. and Rogers, L. J. Lipid Res.,27(4):404–411, 1986. DOI:10.1016/S0022-2275(20)38817-9.
[21] Wang, X. and Kolattukudy, P. E. Biochem. Biophys. Res. Commun.,208(1):210–215, 1995. DOI:10.1006/bbrc.1995.1325. [22] Miklaszewska, M. and Banaś, A. Plant Sci.,249:84–92, 2016. DOI:10.1016/j.plantsci.2016.05.009.
[23] Rowland, O., Zheng, H., Hepworth, S. R., Lam, P., Jetter, R., and Kunst, L. Plant Physiol.,142(3):866–877, 2006. DOI:
10.1104/pp.106.086785.
[24] Hagström, Å. K., Walther, A., Wendland, J., and Löfstedt, C. Insect Biochem. Mol. Biol., 43(6):510–521, 2013. DOI:
10.1016/j.ibmb.2013.03.006.
[25] Burdett, K., Larkins, L. K., Das, A. K., and Hajra, A. K. J. Biol. Chem., 266(19):12201–12206, 1991. DOI: 10.1016/
S0021-9258(18)98881-2.
[26] Cheng, J. B. and Russell, D. W. J. Biol. Chem.,279(36):37789–37797, 2004. DOI:10.1074/jbc.m406225200.
[27] Honsho, M., Asaoku, S., Fukumoto, K., and Fujiki, Y. J. Biol. Chem.,288(48):34588–34598, 2013. DOI:10.1074/jbc.M113.
498345.
[28] Marchler-Bauer, A., Bo, Y., Han, L., He, J., Lanczycki, C. J., Lu, S., Chitsaz, F., Derbyshire, M. K., Geer, R. C., Gonzales, N. R., Gwadz, M., Hurwitz, D. I., Lu, F., Marchler, G. H., Song, J. S., Thanki, N., Wang, Z., Yamashita, R. A., Zhang, D., Zheng, C., Geer, L. Y., and Bryant, S. H. Nucleic Acids Res.,45(D1):D200–D203, 2016. DOI:10.1093/nar/gkw1129. [29] Krogh, A., Larsson, B., von Heijne, G., and Sonnhammer, E. L. L. J. Mol. Biol.,305(3):567–580, 2001. DOI:10.1006/jmbi.
2000.4315.
[30] Moto, K., Yoshiga, T., Yamamoto, M., Takahashi, S., Okano, K., Ando, T., Nakata, T., and Matsumoto, S. Proc. Natl.
Acad. Sci.,100(16):9156–9161, 2003. DOI:10.1073/pnas.1531993100.
[31] Antony, B., Fujii, T., Moto, K., Matsumoto, S., Fukuzawa, M., Nakano, R., Tatsuki, S., and Ishikawa, Y. Insect Biochem.
Mol. Biol.,39(2):90–95, 2009. DOI:10.1016/j.ibmb.2008.10.008.
[32] Domergue, F., Vishwanath, S. J., Joubès, J., Ono, J., Lee, J. A., Bourdon, M., Alhattab, R., Lowe, C., Pascal, S., Lessire, R., and Rowland, O. Plant Physiol.,153(4):1539–1554, 2010. DOI:10.1104/pp.110.158238.
[33] Lassance, J.-M., Groot, A. T., Liénard, M. A., Antony, B., Borgwardt, C., Andersson, F., Hedenström, E., Heckel, D. G., and Löfstedt, C. Nature,466(7305):486–489, 2010. DOI:10.1038/nature09058.
[34] Liénard, M. A., Hagström, A. K., Lassance, J.-M., and Löfstedt, C. Proc. Natl. Acad. Sci.,107(24):10955–10960, 2010.
DOI:10.1073/pnas.1000823107.
[35] Teerawanichpan, P., Robertson, A. J., and Qiu, X. Insect Biochem. Mol. Biol.,40(9):641–649, 2010. DOI:10.1016/j.ibmb.
2010.06.004.
[36] Chen, W., Yu, X.-H., Zhang, K., Shi, J., Oliveira, S. D., Schreiber, L., Shanklin, J., and Zhang, D. Plant Physiol., 157(2):842–853, 2011. DOI:10.1104/pp.111.181693.
[37] Hellenbrand, J., Biester, E.-M., Gruber, J., Hamberg, M., and Frentzen, M. BMC Biochemistry,12(1):64, 2011. DOI:
10.1186/1471-2091-12-64.
[38] Doan, T. T. P., Domergue, F., Fournier, A. E., Vishwanath, S. J., Rowland, O., Moreau, P., Wood, C. C., Carlsson, A. S., Hamberg, M., and Hofvander, P. Biochim. Biophys. Acta Mol. Cell Biol. Lipids,1821(9):1244–1255, 2012. DOI:
10.1016/j.bbalip.2011.10.019.
[39] Hagström, Å. K., Liénard, M. A., Groot, A. T., Hedenström, E., and Löfstedt, C. PLOS One,7(5):e37230, 2012. DOI:
10.1371/journal.pone.0037230.
[40] Teerawanichpan, P. and Qiu, X. Mar. Biotechnol.,14(2):227–236, 2012. DOI:10.1007/s10126-011-9406-3.
[41] Hagström, Å. K., Wang, H.-L., Liénard, M. A., Lassance, J.-M., Johansson, T., and Löfstedt, C. Microb. Cell Fact., 12(1):125, 2013. DOI:10.1186/1475-2859-12-125.
[42] Chacón, M. G., Fournier, A. E., Tran, F., Dittrich-Domergue, F., Pulsifer, I. P., Domergue, F., and Rowland, O. J. Biol.
Chem.,288(42):30345–30355, 2013. DOI:10.1074/jbc.M113.499715.
[43] Lassance, J.-M., Liénard, M. A., Antony, B., Qian, S., Fujii, T., Tabata, J., Ishikawa, Y., and Löfstedt, C. Proc. Natl. Acad.
Sci.,110(10):3967–3972, 2013. DOI:10.1073/pnas.1208706110.
[44] Liénard, M. A., Wang, H.-L., Lassance, J.-M., and Löfstedt, C.Nat. Commun.,5(1):3957, 2014. DOI:10.1038/ncomms4957. [45] Wang, Y., Wang, M., Sun, Y., Wang, Y., Li, T., Chai, G., Jiang, W., Shan, L., Li, C., Xiao, E., and Wang, Z.J. Exp. Bot.,
66(5):1165–1178, 2014. DOI:10.1093/jxb/eru457.
[46] Carot-Sans, G., Munoz, L., Piulachs, M. D., Guerrero, A., and Rosell, G. Insect Mol. Biol., 24(1):82–92, 2015. DOI:
10.1111/imb.12138.
[47] Antony, B., Ding, B.-J., Moto, K., Aldosari, S. A., and Aldawood, A. S.Sci. Rep.,6(1):29927, 2016. DOI:10.1038/srep29927. [48] Cinnamon, E., Makki, R., Sawala, A., Wickenberg, L. P., Blomquist, G. J., Tittiger, C., Paroush, Z., and Gould, A. P.PLOS
Genetics,12(8):e1006154, 2016. DOI:10.1371/journal.pgen.1006154.
[49] Doan, T. T. P., Carlsson, A. S., Stymne, S., and Hofvander, P. Acta Biochim. Pol.,63(3):565–570, 2016. DOI:10.18388/
abp.2016_1245.
[50] Wang, M., Wang, Y., Wu, H., Xu, J., Li, T., Hegebarth, D., Jetter, R., Chen, L., and Wang, Z.Sci. Rep.,6(1), 2016. DOI:
10.1038/srep25008.
[51] Hu, Y.-H., Chen, X.-M., Yang, P., and Ding, W.-F. Arch. Insect Biochem. Physiol.,97(4):e21445, 2017. DOI:10.1002/arch.
21445.
[52] Wang, M., Wu, H., Xu, J., Li, C., Wang, Y., and Wang, Z. Front. Plant Sci.,8:1012, 2017. DOI:10.3389/fpls.2017.01012. [53] Chai, G., Li, C., Xu, F., Li, Y., Shi, X., Wang, Y., and Wang, Z. BMC Plant Biol., 18(1), 2018. DOI: 10.1186/
s12870-018-1256-y.
[54] Wang, Y., Sun, Y., You, Q., Luo, W., Wang, C., Zhao, S., Chai, G., Li, T., Shi, X., Li, C., Jetter, R., and Wang, Z. Plant Cell Physiol.,59(3):527–543, 2018. DOI:10.1093/pcp/pcx211.
[55] Tupec, M., Buček, A., Janoušek, V., Vogel, H., Prchalová, D., Kindl, J., Pavlíčková, T., Wenzelová, P., Jahn, U., Valterová, I., and Pichová, I. eLife,8:e39231, 2019. DOI:10.7554/elife.39231.
[56] Vatanparast, M. and Kim, Y. J. Asia-Pac. Entomol.,22(3):645–654, 2019. DOI:10.1016/j.aspen.2019.04.009.
[57] Dou, X., Zhang, A., and Jurenka, R. Insect Biochem. Mol. Biol.,116:103260, 2020. DOI:10.1016/j.ibmb.2019.103260. [58] Li, D.-T., Dai, Y.-T., Chen, X., Wang, X.-Q., Li, Z.-D., Moussian, B., and Zhang, C.-X.Pest Manag. Sci.,76(7):2304–2315,
2020. DOI:10.1002/ps.5765.
[59] Wei, X., Mao, L., Wei, X., Xia, M., and Xu, C. Hort. Res.,7(1), 2020. DOI:10.1038/s41438-020-0309-1.
[60] Wang, Y., Xu, J., He, Z., Hu, N., Luo, W., Liu, X., Shi, X., Liu, T., Jiang, Q., An, P., Liu, L., Sun, Y., Jetter, R., Li, C., and Wang, Z. Plant J.,106(5):1468–1483, 2021. DOI:10.1111/tpj.15249.
[61] Zhang, S., Wu, S., Niu, C., Liu, D., Yan, T., Tian, Y., Liu, S., Xie, K., Li, Z., Wang, Y., Zhao, W., Dong, Z., Zhu, T., Hou, Q., Ma, B., An, X., Li, J., and Wan, X. J. Exp. Bot.,72(12):4298–4318, 2021. DOI:10.1093/jxb/erab142.
[62] Cha, W. H. and Lee, D.-W. Insect Sci.,29(4):1135–1144, 2022. DOI:10.1111/1744-7917.12999.
[63] Crooks, G. E., Hon, G., Chandonia, J.-M., and Brenner, S. E.Genome Res.,14(6):1188–1190, 2004. DOI:10.1101/gr.849004. [64] Barajas, J. F., Phelan, R. M., Schaub, A. J., Kliewer, J. T., Kelly, P. J., Jackson, D. R., Luo, R., Keasling, J. D., and Tsai,
S.-C. Chem. Biol.,22(8):1018–1029, 2015. DOI:10.1016/j.chembiol.2015.06.022.
[65] Stierand, K., Maass, P. C., and Rarey, M. Bioinformatics,22(14):1710–1716, 2006. DOI:10.1093/bioinformatics/btl150.
[66] Exner, T., Romero-Brey, I., Yifrach, E., Rivera-Monroy, J., Schrul, B., Zouboulis, C. C., Stremmel, W., Honsho, M., Bartenschlager, R., Zalckvar, E., Poppelreuther, M., and Füllekrug, J. J. Cell Sci., 2019. DOI:10.1242/jcs.223016.
[67] Aarts, M., Hodge, R., Kalantidis, K., Florack, D., Wilson, Z., Mulligan, B., Stiekema, W., Scott, R., and Pereira, A. Plant J.,12(3):615–623, 1997. DOI:10.1046/j.1365-313X.1997.d01-8.x.
[68] Rossmann, M. G., Moras, D., and Olsen, K. W. Nature,250(5463):194–199, 1974. DOI:10.1038/250194a0.
[69] Jumper, J., Evans, R., Pritzel, A., Green, T., Figurnov, M., Ronneberger, O., Tunyasuvunakool, K., Bates, R., Žídek, A., Potapenko, A., Bridgland, A., Meyer, C., Kohl, S. A. A., Ballard, A. J., Cowie, A., Romera-Paredes, B., Nikolov, S., Jain, R., Adler, J., Back, T., Petersen, S., Reiman, D., Clancy, E., Zielinski, M., Steinegger, M., Pacholska, M., Berghammer, T., Bodenstein, S., Silver, D., Vinyals, O., Senior, A. W., Kavukcuoglu, K., Kohli, P., and Hassabis, D.Nature,596(7873):583–
589, 2021. DOI:10.1038/s41586-021-03819-2.
[70] Mirdita, M., Schütze, K., Moriwaki, Y., Heo, L., Ovchinnikov, S., and Steinegger, M. Nat. Methods,19:679–682, 2022.
DOI:10.1038/s41592-022-01488-1.
[71] Willis, R. M., Wahlen, B. D., Seefeldt, L. C., and Barney, B. M. Biochemistry,50(48):10550–10558, 2011. DOI:10.1021/
bi2008646.
[72] Nevenzel, J. C. Lipids,5(3):308–319, 1970. DOI:10.1007/BF02531462.
[73] Bjostad, L. B. and Roelofs, W. L. Science,220(4604):1387–1389, 1983. DOI:10.1126/science.220.4604.1387.
[74] Köblös, G., Dankó, T., Sipos, K., Geiger, Á., Szlanka, T., Fodor, J., and Fónagy, A.Gen. Comp. Endocrinol.,221:217–227, 2015. DOI:10.1016/j.ygcen.2015.03.004.
[75] Jirošová, A., Sillam-Dussès, D., Kyjaková, P., Kalinová, B., Dolejšová, K., Jančařík, A., Majer, P., Cristaldo, P. F., and Hanus, R.J. Chem. Ecol.,42(10):1070–1081, 2016. DOI:10.1007/s10886-016-0756-1.
[76] Morse, D. and Meighen, E. J. Chem. Ecol.,12(2):335–351, 1986. DOI:10.1007/BF01020560.
[77] Kullenberg, B., Bergström, G., and Ställberg-Stenhagen, S. Acta Chem. Scand.,24:1481–1483, 1970. DOI: 10.3891/acta.
chem.scand.24-1481.
[78] Pickett, J. A., Williams, I. H., and Martin, A. P. J. Chem. Ecol.,8(1):163–175, 1982. DOI:10.1007/BF00984013. [79] Bergman, P. and Bergström, G. J. Chem. Ecol.,23(5):1235–1251, 1997. DOI:10.1023/B:JOEC.0000006461.69512.33. [80] Urbanová, K., Valterová, I., Hovorka, O., and Kindl, J. Eur. J. Entomol.,98(1):111–115, 2001. DOI:10.14411/eje.2001.017. [81] Arima, R., Takahara, K., Kadoshima, T., Numazaki, F., ando, T., Uchiyama, M., Nagasawa, H., Kitamura, A., and Suzuki,
A. Appl. Entomol. Zool.,26(1):137–147, 1991. DOI:10.1303/aez.26.137.
[82] Fabrias, G., Barrot, M., and Camps, F.Insect Biochem. Mol. Biol.,25(5):655–660, 1995. DOI:10.1016/0965-1748(95)00003-E. [83] Fónagy, A., Moto, K., Ohnishi, A., Kurihara, M., Kis, J., and Matsumoto, S. Gen. Comp. Endocrinol.,172(1):62–76, 2011.
DOI:10.1016/j.ygcen.2011.02.018.
[84] Gu, S.-H., Wu, K.-M., Guo, Y.-Y., Pickett, J. A., Field, L. M., Zhou, J.-J., and Zhang, Y.-J. BMC Genomics,14(1), 2013.
DOI:10.1186/1471-2164-14-636.
[85] Ding, B.-J. and Löfstedt, C. BMC Genomics,16(1), 2015. DOI:10.1186/s12864-015-1909-2.
[86] Zhang, Y.-N., Zhu, X.-Y., Fang, L.-P., He, P., Wang, Z.-Q., Chen, G., Sun, L., Ye, Z.-F., Deng, D.-G., and Li, J.-B.PLOS One,10(10):e0140019, 2015. DOI:10.1371/journal.pone.0140019.
[87] Antony, B., Soffan, A., Jakše, J., Alfaifi, S., Sutanto, K. D., Aldosari, S. A., Aldawood, A. S., and Pain, A.BMC Genomics, 16(1), 2015. DOI:10.1186/s12864-015-1710-2.
[88] Buček, A., Brabcová, J., Vogel, H., Prchalová, D., Kindl, J., Valterová, I., and Pichová, I.Insect Mol. Biol.,25(3):295–314, 2016. DOI:10.1111/imb.12221.
[89] Teerawanichpan, P. and Qiu, X. Lipids,45(3):263–273, 2010. DOI:10.1007/s11745-010-3395-2.
[90] Hofvander, P., Doan, T. T. P., and Hamberg, M. FEBS Lett.,585(22):3538–3543, 2011. DOI:10.1016/j.febslet.2011.10.016. [91] Jaspers, M. H. J., Pflanz, R., Riedel, D., Kawelke, S., Feussner, I., and Schuh, R. Dev. Biol.,385(1):23–31, 2014. DOI:
10.1016/j.ydbio.2013.10.022.
[92] Wang, A., Xia, Q., Xie, W., Dumonceaux, T., Zou, J., Datla, R., and Selvaraj, G. Plant J.,30(6):613–623, 2002. DOI:
10.1046/j.1365-313X.2002.01313.x.
[93] Doan, T. T. P., Carlsson, A. S., Hamberg, M., Bülow, L., Stymne, S., and Olsson, P. J. Plant Physiol.,166(8):787–796, 2009. DOI:10.1016/j.jplph.2008.10.003.
[94] Rowland, O. and Domergue, F. Plant Sci.,193-194:28–38, 2012. DOI:10.1016/j.plantsci.2012.05.002. [95] Miwa, T. K. J. Am. Oil Chem. Soc.,48(6):259–264, 1971. DOI:10.1007/BF02638458.
[96] Honsho, M., Asaoku, S., and Fujiki, Y. J. Biol. Chem.,285(12):8537–8542, 2010. DOI:10.1074/jbc.M109.083311.
[97] Buchert, R., Tawamie, H., Smith, C., Uebe, S., Innes, A. M., Hallak, B. A., Ekici, A. B., Sticht, H., Schwarze, B., Lamont, R. E., Parboosingh, J. S., Bernier, F. P., and Jamra, R. A. Am. J. Hum. Genet., 95(5):602–610, 2014. DOI:
10.1016/j.ajhg.2014.10.003.
[98] Lemoine, F., Correia, D., Lefort, V., Doppelt-Azeroual, O., Mareuil, F., Cohen-Boulakia, S., and Gascuel, O. Nucleic Acids Res.,47(W1):W260–W265, 2019. DOI:10.1093/nar/gkz303.
[99] Moore, R. M., Harrison, A. O., McAllister, S. M., Polson, S. W., and Wommack, K. E. PeerJ,8:e8584, 2020. DOI:
10.7717/peerj.8584.
[100] Liénard, M. A. and Löfstedt, C. Commun. Integr. Biol.,3(6):586–588, 2010. DOI:10.4161/cib.3.6.13177.
[101] Stubbs, C. D. and Smith, A. D.Biochim. Biophys. Acta Biomembr.,779(1):89–137, 1984. DOI:10.1016/0304-4157(84)90005-4. [102] Spector, A. A. and Yorek, M. A. J. Lipid Res.,26(9):1015–1035, 1985. DOI:10.1016/S0022-2275(20)34276-0.
[103] Hazel, J.Prog. Lipid Res.,29(3):167–227, 1990. DOI:10.1016/0163-7827(90)90002-3.
[104] Zhang, Y.-M. and Rock, C. O. Nat. Rev. Microbiol.,6(3):222–233, 2008. DOI:10.1038/nrmicro1839.
[105] Kazaz, S., Miray, R., Lepiniec, L., and Baud, S. Prog. Lipid Res.,85:101138, 2022. DOI:10.1016/j.plipres.2021.101138. [106] Solomon, E. I., Brunold, T. C., Davis, M. I., Kemsley, J. N., Lee, S.-K., Lehnert, N., Neese, F., Skulan, A. J., Yang, Y.-S.,
and Zhou, J. Chem. Rev.,100(1):235–350, 2000. DOI:10.1021/cr9900275.
[107] Krebs, C., Bollinger, J. M., and Booker, S. J. Current Opinion in Chemical Biology,15(2):291–303, 2011. DOI:10.1016/j.
cbpa.2011.02.019.
[108] Jasniewski, A. J. and Que, L. Chem. Rev.,118(5):2554–2592, 2018. DOI:10.1021/acs.chemrev.7b00457.
[109] Khider, M. L. K., Brautaset, T., and Irla, M.World J. Microbiol. Biotechnol.,37(4), 2021. DOI:10.1007/s11274-021-03038-x. [110] Shanklin, J., Guy, J. E., Mishra, G., and Lindqvist, Y. J. Biol. Chem., 284(28):18559–18563, 2009. DOI: 10.1074/jbc.
R900009200.
[111] Nachtschatt, M., Okada, S., and Speight, R.Eur. J. Lipid Sci. Technol.,122(12):2000181, 2020. DOI:10.1002/ejlt.202000181. [112] Halim, N. F. A. A., Ali, M. S. M., Leow, A. T. C., and Rahman, R. N. Z. R. A.Appl. Microbiol. Biotechnol., (106):5957–5972,
2022. DOI:10.1007/s00253-022-12142-3.
[113] Shanklin, J., Whittle, E., and Fox, B. G.Biochemistry,33(43):12787–12794, 1994. DOI:10.1021/bi00209a009.
[114] Broun, P., Shanklin, J., Whittle, E., and Somerville, C.Science,282(5392):1315–1317, 1998. DOI:10.1126/science.282.5392.
1315.
[115] Lee, M., Lenman, M., Banaś, A., Bafor, M., Singh, S., Schweizer, M., Nilsson, R., Liljenberg, C., Dahlqvist, A., Gummeson, P.-O., Sjödahl, S., Green, A., and Stymne, S. Science,280(5365):915–918, 1998. DOI:10.1126/science.280.5365.915.
[116] Broadwater, J. A., Whittle, E., and Shanklin, J. J. Biol. Chem.,277(18):15613–15620, 2002. DOI:10.1074/jbc.M200231200. [117] Cahoon, E. B. and Kinney, A. J. J. Biol. Chem.,279(13):12495–12502, 2004. DOI:10.1074/jbc.M314329200.
[118] Zhu, G., Koszelak-Rosenblum, M., Connelly, S. M., Dumont, M. E., and Malkowski, M. G. J. Biol. Chem.,290(50):29820–
29833, 2015. DOI:10.1074/jbc.M115.680124.
[119] Man, W. C., Miyazaki, M., Chu, K., and Ntambi, J. M.J. Biol. Chem.,281(2):1251–1260, 2006. DOI:10.1074/jbc.M508733200. [120] Bai, Y., McCoy, J. G., Levin, E. J., Sobrado, P., Rajashankar, K. R., Fox, B. G., and Zhou, M. Nature,524(7564):252–256,
2015. DOI:10.1038/nature14549.
[121] Royer, J., Shanklin, J., Balch-Kenney, N., Mayorga, M., Houston, P., de Jong, R. M., McMahon, J., Laprade, L., Blomquist, P., Berry, T., Cai, Y., LoBuglio, K., Trueheart, J., and Chevreux, B. Sci. Adv.,6(17), 2020. DOI:10.1126/sciadv.aay9226. [122] Bloomfield, D. K. and Bloch, K. J. Biol. Chem.,235(2):337–345, 1960. DOI:10.1016/S0021-9258(18)69525-0.
[123] Borgeson, C. E., de Renobales, M., and Blomquist, G. J. Biochim. Biophys. Acta,1047(2):135–140, 1990. DOI:10.1016/
0005-2760(90)90039-z.
[124] Goren, M. A. and Fox, B. G. Protein Expr. Purif.,62(2):171–178, 2008. DOI:10.1016/j.pep.2008.08.002.
[125] Shen, J., Wu, G., Tsai, A.-L., and Zhou, M.J. Mol. Biol.,432(18):5152–5161, 2020. DOI:10.1016/j.jmb.2020.05.017.
[126] Shen, J., Wu, G., Tsai, A.-L., and Zhou, M.Commun. Biol.,5(1), 2022. DOI:10.1038/s42003-022-03882-z.
[127] Stukey, J. E., McDonough, V. M., and Martin, C. E.J. Biol. Chem.,265(33):20144–20149, 1990. DOI:10.1016/S0021-9258(17) 30481-7.
[128] Knipple, D. C., Rosenfield, C.-L., Miller, S. J., Liu, W., Tang, J., Ma, P. W. K., and Roelofs, W. L. Proc. Natl. Acad. Sci., 95(26):15287–15292, 1998. DOI:10.1073/pnas.95.26.15287.
[129] Peyou-Ndi, M. M., Watts, J. L., and Browse, J.Arch. Biochem. Biophys.,376(2):399–408, 2000. DOI:10.1006/abbi.2000.1733. [130] Moto, K., Suzuki, M. G., Hull, J. J., Kurata, R., Takahashi, S., Yamamoto, M., Okano, K., Imai, K., Ando, T., and
Matsumoto, S. Proc. Natl. Acad. Sci.,101(23):8631–8636, 2004. DOI:10.1073/pnas.0402056101.
[131] Buček, A., Matoušková, P., Sychrová, H., Pichová, I., and Hrušková-Heidingsfeldová, O. PLOS One,9(3):e93322, 2014.
DOI:10.1371/journal.pone.0093322.
[132] Buček, A., Matoušková, P., Vogel, H., Šebesta, P., Jahn, U., Weißflog, J., Svatoš, A., and Pichová, I. Proc. Natl. Acad.
Sci.,112(41):12586–12591, 2015. DOI:10.1073/pnas.1514566112.
[133] Knipple, D. C., Rosenfield, C.-L., Nielsen, R., You, K. M., and Jeong, S. E. Genetics,162(4):1737–1752, 2002. DOI:
10.1093/genetics/162.4.1737.
[134] Hashimoto, K., Yoshizawa, A. C., Okuda, S., Kuma, K., Goto, S., and Kanehisa, M. J. Lipid Res.,49(1):183–191, 2008.
DOI:10.1194/jlr.M700377-JLR200.
[135] Lou, Y. and Shanklin, J. J. Biol. Chem.,285(25):19384–19390, 2010. DOI:10.1074/jbc.M110.125377. [136] Meesapyodsuk, D. and Qiu, X. ACS Chem. Biol.,9(4):922–934, 2014. DOI:10.1021/cb400675d.
[137] Wang, H., Klein, M. G., Zou, H., Lane, W., Snell, G., Levin, I., Li, K., and Sang, B.-C.Nat. Struct. Mol. Biol.,22(7):581–585, 2015. DOI:10.1038/nsmb.3049.
[138] Wilding, M., Nachtschatt, M., Speight, R., and Scott, C. Mol. Phylogenet. Evol.,115:50–57, 2017. DOI:10.1016/j.ympev.
2017.07.012.
[139] Cai, Y., Yu, X.-H., Chai, J., Liu, C.-J., and Shanklin, J.J. Biol. Chem.,295(32):11337–11345, 2020. DOI:10.1074/jbc.RA120.
014258.
[140] Behrouzian, B. and Buist, P. H. Curr. Opin. Chem. Biol.,6(5):577–582, 2002. DOI:10.1016/S1367-5931(02)00365-4. [141] Petroff, A. B., Weir, R. L., Yates, C. R., Ng, J. D., and Baudry, J. Biomolecules, 11(10):1435, 2021. DOI: 10.3390/
biom11101435.
[142] Nagao, K., Murakami, A., and Umeda, M. Chem. Pharm. Bull.,67(4):327–332, 2019. DOI:10.1248/cpb.c18-01001. [143] Matoušková, P., Pichová, I., and Svatoš, A.Insect Biochem. Mol. Biol.,37(6):601–610, 2007. DOI:10.1016/j.ibmb.2007.03.004. [144] Lassance, J.-M., Ding, B.-J., and Löfstedt, C. BMC Biology,19(1):83, 2021. DOI:10.1186/s12915-021-01001-8.
[145] Serra, M., Piña, B., Abad, J. L., Camps, F., and Fabriàs, G. Proc. Natl. Acad. Sci.,104(42):16444–16449, 2007. DOI:
10.1073/pnas.0705385104.
[146] Fujii, T., Ito, K., Tatematsu, M., Shimada, T., Katsuma, S., and Ishikawa, Y. Proc. Natl. Acad. Sci.,108(17):7102–7106, 2011. DOI:10.1073/pnas.1019519108.
[147] Buček, A., Vogel, H., Matoušková, P., Prchalová, D., Žáček, P., Vrkoslav, V., Šebesta, P., Svatoš, A., Jahn, U., Valterová, I., and Pichová, I. Insect Biochem. Mol. Biol.,43(8):724–731, 2013. DOI:10.1016/j.ibmb.2013.05.003.
[148] Ding, B.-J., Carraher, C., and Löfstedt, C. Insect Biochem. Mol. Biol.,74:68–75, 2016. DOI:10.1016/j.ibmb.2016.05.002. [149] Ding, B.-J., Hofvander, P., Wang, H.-L., Durrett, T. P., Stymne, S., and Löfstedt, C.Nat. Commun.,5(1):3353, 2014. DOI:
10.1038/ncomms4353.
[150] Liu, W., Ma, P. W., Marsella-Herrick, P., Rosenfield, C. L., Knipple, D. C., and Roelofs, W. Insect Biochem. Mol. Biol., 29(5):435–43, 1999. DOI:10.1016/s0965-1748(99)00020-x.
[151] Hao, G., Liu, W., O’Connor, M., and Roelofs, W. L. Insect Biochem. Mol. Biol.,32(9):961–966, 2002. DOI: 10.1016/
s0965-1748(01)00176-x.
[152] Liénard, M. A., Lassance, J.-M., Wang, H.-L., Zhao, C.-H., Piskur, J., Johansson, T., and Löfstedt, C.Insect Biochem. Mol.
Biol.,40(6):440–452, 2010. DOI:10.1016/j.ibmb.2010.04.003.
[153] Albre, J., Liénard, M. A., Sirey, T. M., Schmidt, S., Tooman, L. K., Carraher, C., Greenwood, D. R., Löfstedt, C., and Newcomb, R. D. PLoS Genetics,8(1):e1002489, 2012. DOI:10.1371/journal.pgen.1002489.
[154] Jaworski, J. G. and Stumpf, P. K.Arch. Biochem. Biophys.,162(1):158–165, 1974. DOI:10.1016/0003-9861(74)90114-3. [155] Mckeon, T. A. and Stumpf, P. K.J. Biol. Chem.,257(20):2141–2147, 1982. DOI:10.1016/S0021-9258(18)33690-1.
[156] Thompson, G. A., Scherer, D. E., Aken, S. F.-V., Kenny, J. W., Young, H. L., Shintani, D. K., Kridl, J. C., and Knauf, V. C.
Proc. Natl. Acad. Sci.,88:2578–2582, 1991. DOI:10.1073/pnas.88.6.2578.
[157] Schultz, D. J., Suh, M. C., and Ohlrogge, J. B. Plant Physiol.,124(2):681–692, 2000. DOI:10.1104/pp.124.2.681.
[158] Cahoon, E. B., Coughlan, S. J., and Shanklin, J.Plant Mol. Biol.,33(6):1105–1110, 1997. DOI:10.1023/a:1005821007291. [159] Lindqvist, Y. Encyclopedia of Inorganic and Bioinorganic Chemistry, chapter Delta9 Stearoyl-ACP desaturase. John Wiley
and Sons, 2011.
[160] Shanklin, J. and Somerville, C.Proc. Natl. Acad. Sci.,88(6):2510–2514, 1991. DOI:10.1073/pnas.88.6.2510.
[161] Liu, Q., Chai, J., Moche, M., Guy, J., Lindqvist, Y., and Shanklin, J. Plant Physiol., 169(1):432–441, 2015. DOI:
10.1104/pp.15.00622.
[162] Guy, J. E., Whittle, E., Moche, M., Lengqvist, J., Lindqvist, Y., and Shanklin, J. Proc. Natl. Acad. Sci.,108(40):16594–
16599, 2011. DOI:10.1073/pnas.1110221108.
[163] Lindqvist, Y., Huang, W. J., Schneider, G., and Shanklin, J. EMBO J.,15(16):4081–4092, 1996. DOI:10.1002/j.1460-2075.
1996.tb00783.x.
[164] Moche, M., Shanklin, J., Ghoshal, A., and Lindqvist, Y. J. Biol. Chem.,278(27):25072–25080, 2003. DOI:10.1074/jbc.
M301662200.
[165] Guy, J. E., Abreu, I. A., Moche, M., Lindqvist, Y., Whittle, E., and Shanklin, J.Proc. Natl. Acad. Sci.,103(46):17220–17224, 2006. DOI:10.1073/pnas.0607165103.
[166] Guy, J. E., Whittle, E., Kumaran, D., Lindqvist, Y., and Shanklin, J. J. Biol. Chem.,282(27):19863–19871, 2007. DOI:
10.1074/jbc.M702520200.
[167] Sobrado, P., Lyle, K. S., Kaul, S. P., Turco, M. M., Arabshahi, I., Marwah, A., and Fox, B. G. Biochemistry,45(15):4848–
4858, 2006. DOI:10.1021/bi0600547.
[168] Broadwater, J. A., Laundre, B. J., and Fox, B. G.J. Inorg. Biochem.,78(1):7–14, 2000. DOI:10.1016/s0162-0134(99)00199-3. [169] Haas, J. A. and Fox, B. G. Biochemistry,38(39):12833–12840, 1999. DOI:10.1021/bi991318a.
[170] Guy, J. E., Cai, Y., Baer, M. D., Whittle, E., Chai, J., Yu, X.-H., Lindqvist, Y., Raugei, S., and Shanklin, J.Plant Physiol., 188(3):1537–1549, 2022. DOI:10.1093/plphys/kiab577.
[171] Cahoon, E. B., Lindqvist, Y., Schneider, G., and Shanklin, J. Proc. Natl. Acad. Sci., 94(10):4872–4877, 1997. DOI:
10.1073/pnas.94.10.4872.
[172] Whittle, E. and Shanklin, J.J. Biol. Chem.,276(24):21500–21505, 2001. DOI:10.1074/jbc.M102129200.
[173] Cahoon, E. B., Shah, S., Shanklin, J., and Browse, J.Plant Physiol.,117(2):593–598, 1998. DOI:10.1104/pp.117.2.593.
[174] Sedeek, K. E. M., Whittle, E., Guthörl, D., Grossniklaus, U., Shanklin, J., and Schlüter, P. M.Curr. Biol.,26(11):1505–1511, 2016. DOI:10.1016/j.cub.2016.04.018.
[175] Yang, Y.-S., Broadwater, J. A., Pulver, S. C., Fox, B. G., and Solomon, E. I.J. Am. Chem. Soc.,121(12):2770–2783, 1999.
DOI:10.1021/ja9822714.
[176] Broadwater, J. A., Achim, C., Munck, E., and Fox, B. G.Biochemistry,38(38):12197–12204, 1999. DOI:10.1021/bi9914199. [177] Siegbahn, P. E. M.Inorg. Chem.,38(12):2880–2889, 1999. DOI:10.1021/ic981332w.
[178] Han, W. G. and Noodleman, L.Inorg. Chem.,47(8):2975–2986, 2008. DOI:10.1021/ic701194b.
[179] Jensen, K. P., Bell, C. B., Clay, M. D., and Solomon, E. I. J. Am. Chem. Soc., 131(34):12155–12171, 2009. DOI:
10.1021/ja809983g.
[180] Han, W. G. and Noodleman, L.Dalton Trans., (30):6045–6057, 2009. DOI:10.1039/b903847g.
[181] Bochevarov, A. D., Friesner, R. A., and Lippard, S. J. J. Chem. Theory Comput.,6(12):3735–3749, 2010. DOI:10.1021/
ct100398m.
[182] Bochevarov, A. D., Li, J. N., Song, W. J., Friesner, R. A., and Lippard, S. J.J. Am. Chem. Soc.,133(19):7384–7397, 2011.
DOI:10.1021/ja110287y.
[183] Han, W. G. and Noodleman, L.Inorg. Chem.,50(6):2302–2320, 2011. DOI:10.1021/ic1020127.
[184] Srnec, M., Rokob, T. A., Schwartz, J. K., Kwak, Y., Rulíšek, L., and Solomon, E. I. Inorg. Chem.,51(5):2806–2820, 2012.
DOI:10.1021/ic2018067.
[185] Rokob, T. A.J. Am. Chem. Soc.,138(44):14623–14638, 2016. DOI:10.1021/jacs.6b06987.
[186] Fox, B. G., Lyle, K. S., and Rogge, C. E. Acc. Chem. Res.,37(7):421–429, 2004. DOI:10.1021/ar030186h.
[187] Behrouzian, B., Savile, C. K., Dawson, B., Buist, P. H., and Shanklin, J. J. Am. Chem. Soc.,124(13):3277–3278, 2002.
DOI:10.1021/ja012252l.
[188] Lyle, K. S., Haas, J. A., and Fox, B. G. Biochemistry,42(19):5857–5866, 2003. DOI:10.1021/bi030020o.
[189] Broadwater, J. A., Ai, J. Y., Loehr, T. M., Sanders-Loehr, J., and Fox, B. G. Biochemistry,37(42):14664–14671, 1998.
DOI:10.1021/bi981839i.
[190] Chalupský, J., Rokob, T. A., Kurashige, Y., Yanai, T., Solomon, E. I., Rulíšek, L., and Srnec, M. J. Am. Chem. Soc., 136(45):15977–15991, 2014. DOI:10.1021/ja506934k.
[191] Bím, D., Chalupský, J., Culka, M., Solomon, E. I., Rulíšek, L., and Srnec, M. J. Am. Chem. Soc.,142(23):10412–10423, 2020. DOI:10.1021/jacs.0c01786.
[192] Nagai, J. and Bloch, K. J. Biol. Chem.,243(17):4626–4633, 1968. DOI:10.1016/S0021-9258(18)93235-7. [193] Schmidt, H. and Heinz, E. Plant Physiol.,94(1):214–220, 1990. DOI:10.1104/pp.94.1.214.
[194] Wada, H., Schmidt, H., Heinz, E., and Murata, N. J. Bacteriol.,175(2):544–547, 1993. DOI:10.1128/Jb.175.2.544-547.1993. [195] Morris, L. J. Biochem. J.,118(5):681–693, 1970. DOI:10.1042/bj1180681g.
[196] Fox, B. G., Shanklin, J., Somerville, C., and Münck, E. Proc. Natl. Acad. Sci.,90(6):2486–2490, 1993. DOI:10.1073/pnas.
90.6.2486.
[197] Cahoon, E. B., Cranmer, A. M., Shanklin, J., and Ohlrogge, J. B. J. Biol. Chem.,269(44):27519–27526, 1994. DOI:
10.1016/S0021-9258(18)47015-9.
[198] Hoffman, B. J., Broadwater, J. A., Johnson, P., Harper, J., Fox, B. G., and Kenealy, W. R.Protein Expr. Purif.,6(5):646–654, 1995. DOI:10.1006/prep.1995.1085.
[199] Cahoon, E. B. and Shanklin, J. Proc. Natl. Acad. Sci.,97(22):12350–12355, 2000. DOI:10.1073/pnas.21027629.
[200] Whittle, E., Cahoon, E. B., Subrahmanyam, S., and Shanklin, J. J. Biol. Chem., 280(31):28169–28176, 2005. DOI:
10.1074/jbc.M504205200.
[201] Liu, B., Sun, Y., Xue, J., Mao, X., Jia, X., and Li, R. Front. Plant Sci., 2019. DOI:10.3389/fpls.2019.00703.
[202] Li, L., Li, Y., Wang, R., Chao, L., Xiu, Y., and Wang, H.Phytochemistry,178:112480, 2020. DOI:10.1016/j.phytochem.2020.
112480.
[203] Behrouzian, B., Dawson, B., Buist, P. H., and Shanklin, J. Chem. Commun., (8):765–6, 2001. DOI:10.1039/b100035g. [204] Rogge, C. E. and Fox, B. G. Biochemistry,41(31):10141–10148, 2002. DOI:10.1021/bi020306d.
[205] White, R. D. and Fox, B. G. Biochemistry,42(25):7828–7835, 2003. DOI:10.1021/bi030082e.
[206] Whittle, E. J., Tremblay, A. E., Buist, P. H., and Shanklin, J. Proc. Natl. Acad. Sci.,105(38):14738–14743, 2008. DOI:
10.1073/pnas.0805645105.
[207] Whittle, E. J., Cai, Y., Keereetaweep, J., Chai, J., Buist, P. H., and Shanklin, J.Plant Physiol.,182(2):730–738, 2020. DOI:
10.1104/pp.19.01111.
[208] Baier, F., Copp, J. N., and Tokuriki, N.Biochemistry,55(46):6375–6388, 2016. DOI:10.1021/acs.biochem.6b00723. [209] Calam, D. H.Nature,221(5183):856–857, 1969. DOI:10.1038/221856a0.
[210] Lanne, B. S., Bergström, G., Wassgren, A.-B., and Törnbäck, B. Compar. Biochem. and Physiol. B Compar. Biochem., 88(2):631–636, 1987. DOI:10.1016/0305-0491(87)90355-5.
[211] Bergström, G., Bergman, P., Appelgren, M., and Schmidt, J. O. Bioorg. Med. Chem.,4(3):515–519, 1996. DOI:10.1016/
0968-0896(96)00034-X.
[212] Bergman, P., Bergström, G., and Appelgren, M.Chemoecology,7(3):140–145, 1996. DOI:10.1007/BF01245966.
[213] Žáček, P., Kalinová, B., Šobotník, J., Hovorka, O., Ptáček, V., Coppée, A., Verheggen, F., and Valterová, I.J. Chem. Ecol., 35(6):698–705, 2009. DOI:10.1007/s10886-009-9650-4.
[214] Bertsch, A. and Schweer, H. Biochem. Syst. Ecol.,40:103–111, 2012. DOI:10.1016/j.bse.2011.10.009.
[215] Brasero, N., Martinet, B., Lecocq, T., Lhomme, P., Biella, P., Valterová, I., Urbanová, K., Cornalba, M., Hines, H., and Rasmont, P. Insect Sci.,25(1):75–86, 2017. DOI:10.1111/1744-7917.12408.
[216] Kubo, R., ichi Harano, K., and Ono, M.Sci. Nature,104(9-10), 2017. DOI:10.1007/s00114-017-1493-1.
[217] Martinet, B., Lecocq, T., Brasero, N., Biella, P., Urbanová, K., Valterová, I., Cornalba, M., Gjershaug, J. O., Michez, D., and Rasmont, P.Syst. Entomol.,43(1):200–217, 2018. DOI:10.1111/syen.12268.
[218] Brasero, N., Ghisbain, G., Lecocq, T., Michez, D., Valterová, I., Biella, P., Monfared, A., Williams, P. H., Rasmont, P., and Martinet, B. Zoologica Scripta,50(5):616–632, 2021. DOI:10.1111/zsc.12486.
[219] Ayasse, M. and Jarau, S. Annu. Rev. Entomol.,59(1):299–319, 2014. DOI:10.1146/annurev-ento-011613-161949.
[220] Valterová, I., Martinet, B., Michez, D., Rasmont, P., and Brasero, N. Z. Naturforsch. C,74(9-10):233–250, 2019. DOI:
10.1515/znc-2019-0003.
[221] Prchalová, D., Buček, A., Brabcová, J., Žáček, P., Kindl, J., Valterová, I., and Pichová, I. ChemBioChem,17(3):260–267, 2015. DOI:10.1002/cbic.201500415.
[222] Cai, Y., Yu, X.-H., Liu, Q., Liu, C.-J., and Shanklin, J.J. Biol. Chem.,293(51):19844–19853, 2018. DOI:10.1074/jbc.RA118.
005972.
[223] Li, D., Damry, A. M., Petrie, J. R., Vanhercke, T., Singh, S. P., and Jackson, C. J.Biochemistry,59(14):1398–1409, 2020.
DOI:10.1021/acs.biochem.0c00110.
[224] Cui, J., Chen, H., Tang, X., Zhang, H., Chen, Y. Q., and Chen, W. AMB Express, 12(1), 2022. DOI: 10.1186/
s13568-022-01410-0.
[225] Cui, J., Chen, H., Tang, X., Zhang, H., Chen, Y. Q., and Chen, W. Biochem. Biophys. Res. Commun.,586:74–80, 2022.
DOI:10.1016/j.bbrc.2021.11.050.
[226] Garba, L., Yussoff, M. A. M., Halim, K. B. A., Ishak, S. N. H., Ali, M. S. M., Oslan, S. N., and Rahman?, R. N. Z. R. A.
PeerJ, 2018. DOI:10.7717/peerj.4347.
[227] Werner, E. R., Fernández-Quintero, M. L., Hulo, N., Golderer, G., Sailer, S., Lackner, K., Werner-Felmayer, G., Liedl, K. R., and Watschinger, K. Cell. Mol. Life Sci.,79(4), 2022. DOI:10.1007/s00018-022-04238-w.
[228] Xu, Y., Wang, X., Zhang, C., Zhou, X., Xu, X., Han, L., Lv, X., Liu, Y., Liu, S., Li, J., Du, G., Chen, J., Ledesma-Amaro, R., and Liu, L.Nat. Commun.,13(1), 2022. DOI:10.1038/s41467-022-30826-2.
[229] Buček, A., Vazdar, M., Tupec, M., Svatoš, A., and Pichová, I. Comput. Struct. Biotechnol. J.,18:1202–1209, 2020. DOI:
10.1016/j.csbj.2020.05.011.
[230] Liu, W., Jiao, H., O’Connor, M., and Roelofs, W. L. Insect. Biochem. Mol. Biol.,32(11):1489–1495, 2002. DOI:10.1016/
S0965-1748(02)00069-3.
[231] Liu, W., Jiao, H., Murray, N. C., O’Connor, M., and Roelofs, W. L. Proc. Natl. Acad. Sci.,99(2):620–624, 2002. DOI:
10.1073/pnas.221601498.
[232] Kubyshkin, V.Org. Biomol. Chem.,19(32):7031–7040, 2021. DOI:10.1039/D1OB01213D.
[233] Elango, N. A., Radhakrishnan, R., Froland, W. A., Wallar, B. J., Earhart, C. A., Lipscomb, J. D., and Ohlendorf, D. H.
Protein Sci.,6(3):556–568, 1997. DOI:10.1002/pro.5560060305.
[234] Tupec, M., Culka, M., Machara, A., Macháček, S., Bím, D., Svatoš, A., Rulíšek, L., and Pichová, I. Comput. Struct.
Biotechnol. J.,20:1378–1388, 2022. DOI:10.1016/j.csbj.2022.03.010.
[235] Jin, Y. and Lipscomb, J. D. J. Biol. Inorg. Chem.,6(7):717–725, 2001. DOI:10.1007/s007750100250.
[236] Borodina, I., Holkenbrink, C., Dam, M. I., Löfstedt, C., Ding, B., and Wang, H.-L. Method for production of moth pheromones in yeast. WO/2016/207339., 2016.
[237] Effendi, L., Meinhold, P., Wampler, K., Coelho, P., Sheppard, M., and Heel, T. Microorganisms for the production of insect pheromones and related compounds. WO/2017/087846., 2017.
[238] Borodina, I., Holkenbrink, C., Dam, M. I., and Löfstedt, C. Methods for producing fatty alcohols and derivatives thereof in yeast. WO/2018/109163., 2018.
[239] Borodina, I., Holkenbrink, C., Dam, M. I., Löfstedt, C., Ding, B., and Wang, H.-L. Production of desaturated fatty alcohols and desaturated fatty acyl acetates in yeast. WO/2018/109167., 2018.
[240] Ding, B., Löfstedt, C., Borodina, I., Wenning, L., Holkenbrink, C., Kildegaard, K. R., and Petkevicius, K. Methods and cell factories for producing insect pheromones. WO/2020/169389., 2020.
[241] Tupec, M., Buček, A., Valterová, I., and Pichová, I. Z. Naturforsch. C,72:387–403, 2017. DOI:10.1515/znc-2017-0031.
All protein models were generated inChimeraXorPyMOL. The illustration ofOrcinus orcawas modified from an artwork by Matthew Gates.
Supplements
Publication I
Michal Tupec, Aleš Buček, Václav Janoušek, Heiko Vogel, Darina Pr- chalová, Jiří Kindl, Tereza Pavlíčková, Petra Wenzelová, Ullrich Jahn, Irena Valterová, Iva Pichová:
Expansion of the fatty acyl reductase gene family shaped pheromone communication in Hymenoptera.
eLife . 2019, 8 :e39231.
Supporting information is available at URL:https://doi.org/10.7554/eLife.39231.