Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.
Nanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran.
Sci Rep. 2022 Jul 26;12(1):12713. doi: 10.1038/s41598-022-16291-3.
The Candida antarctica lipase B (Novozym 435) is found to catalyze a novel decarboxylative Michael addition in vinylogous carbamate systems for the synthesis of 1,4-benzoxazinone derivatives. The reaction goes through Michael addition, ester hydrolysis and decarboxylation. A possible mechanism is suggested, with simultaneous lipase-catalyzed Michael addition and ester hydrolysis. The present methodology offers formation of complex products through multi-step reactions in a one pot process under mild and facile reaction conditions with moderate to high yields (51-90%) and no side product formation. The reaction seems to be is a great example of enzymatic promiscuity.
南极假丝酵母脂肪酶 B（诺维信 435）被发现可催化乙烯基碳酸酯体系中的新型脱羧迈克尔加成反应，用于合成 1,4-苯并恶嗪酮衍生物。该反应经历迈克尔加成、酯水解和脱羧。提出了一种可能的机制，同时进行脂肪酶催化的迈克尔加成和酯水解。本方法在温和、简便的反应条件下，通过一锅法多步反应形成复杂产物，产率中等至较高（51-90%），无副产物生成。该反应似乎是酶的混杂性的一个很好的例子。
