Oxidation of chiral 9-fluorinated substrates by castor stearoyl-ACP Δ9 desaturase yields novel products

被引:7
作者
Behrouzian, B
Dawson, B
Buist, PH
Shanklin, J
机构
[1] Carleton Univ, Dept Chem, Ottawa, ON K1S 5B6, Canada
[2] Brookhaven Natl Lab, Dept Biol, Upton, NY 11973 USA
[3] Hlth Canada, Div Res Serv, Hlth Prod & Food Branch, Ottawa, ON K1A 0L2, Canada
关键词
D O I
10.1039/b100035g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Desaturation of (S)-9-fluorostearoyl-ACP using stearoyl-ACP Delta (9) desaturase yielded mainly (E)-9-fluoroalk-9-enic product, while desaturation of (R)-9-fluorostearoyl-ACP gave the novel (Z)-9-fluoroalk-9-ene and (Z)-9-fluoroalk-10-ene.
引用
收藏
页码:765 / 766
页数:2
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