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周环化 prenylation:通过 Claisen 重排进行肽修饰。

Pericyclic prenylation: peptide modification through a Claisen rearrangement.

机构信息

Department of Medicinal Chemistry and Molecular Pharmacology, The Purdue University Center for Cancer Research, West Lafayette, IN 47906, USA.

出版信息

Chembiochem. 2011 Dec 16;12(18):2723-6. doi: 10.1002/cbic.201100612. Epub 2011 Nov 24.

Abstract

LynF prenylates, but the prenyl migrates: Schmidt and co-workers have demonstrated that LynF from Lyngbya aestuarii is a reverse O-prenyl transferase. However, a forward C-prenylated product is obtained through a non-enzymatic Claisen rearrangement. The elucidation of this unprecedented two-step process is a significant contribution to our understanding of the biosynthesis of complex macrocyclic peptides.

摘要

LynF 进行 prenyl 化,但 prenyl 发生迁移:Schmidt 及其同事已经证明,来自 Lyngbya aestuarii 的 LynF 是一种反向 O-prenyl 转移酶。然而,通过非酶促的 Claisen 重排得到了正向 C-prenylated 产物。对这一前所未有的两步过程的阐明,是对我们理解复杂大环肽生物合成的重大贡献。

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