Departamento de Química Biológica y Modelización Molecular, Instituto de Química Avanzada de Cataluña IQAC-CSIC, Jordi Girona 18-26, 08034, Barcelona, Spain.
Université Clermont Auvergne, CNRS, SIGMA Clermont, Institut de Chimie de Clermont-Ferrand, 63000, Clermont-Ferrand, France.
Chemistry. 2017 Apr 11;23(21):5005-5009. doi: 10.1002/chem.201701020. Epub 2017 Mar 29.
d-Fructose-6-phosphate aldolase (FSA) was probed for extended nucleophile promiscuity by using a series of fluorogenic substrates to reveal retro-aldol activity. Four nucleophiles ethanal, propanone, butanone, and cyclopentanone were subsequently confirmed to be non-natural substrates in the synthesis direction using the wild-type enzyme and its D6H variant. This exceptional widening of the nucleophile substrate scope offers a rapid entry, in good yields and high stereoselectivity, to less oxygenated alkyl ketones and aldehydes, which was hitherto impossible.
通过使用一系列荧光底物来探测 d-果糖-6-磷酸醛缩酶 (FSA) 的扩展亲核试剂混杂性，揭示了反醛缩酶活性。随后使用野生型酶及其 D6H 变体证实了四种亲核试剂乙醛、丙酮、丁酮和环戊酮在合成方向上是非天然底物。这种亲核试剂底物范围的异常扩大，为低氧化度的烷基酮和醛提供了快速进入的途径，产率高，立体选择性好，这在以前是不可能的。
