厘清海洋海绵来源的酰化二肽类纤毛肽的构型分配问题。

Resolution of the Confusion in the Assignments of Configuration for the Ciliatamides, Acylated Dipeptides from Marine Sponges.

机构信息

Laboratory of Aquatic Natural Products Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo , Bunkyo-ku, Tokyo 113-8657, Japan.

出版信息

J Nat Prod. 2017 Oct 27;80(10):2845-2849. doi: 10.1021/acs.jnatprod.7b00684. Epub 2017 Oct 10.

DOI:10.1021/acs.jnatprod.7b00684

PMID:29016113

Abstract

Direct comparison of authentic ciliatamide A with four synthetic isomers (1-4) by means of NMR and chiral-phase HPLC revealed that ciliatamide A possesses the 12R (d-N-MePhe residue) and 22S (l-Lys residue) configurations, which were not identical with either our previous assignment or those proposed by others through total synthesis. The absolute configuration of the methionine sulfoxide residue in ciliatamide D was also revised to be d.

摘要

通过 NMR 和手性相 HPLC 的直接比较，证实了 ciliate 酰胺 A 与四种合成异构体（1-4）的真实性，ciliate 酰胺 A 具有 12R（d-N-MePhe 残基）和 22S（l-Lys 残基）的构型，这与我们之前的分配或通过全合成提出的其他构型都不相同。ciliate 酰胺 D 中蛋氨酸亚砜残基的绝对构型也被修正为 d。