A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid
A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid
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DOI：
10.1002/psc.306
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发表时间：
2001-05-01
影响因子：
2.1
通讯作者：
Kessler, H
中科院分区：
文献类型：
--
作者：
Bayer, T;Riemer, C;Kessler, H
提出了一种新的合成UGI四组分缩合的正交化保护二氨基戊二酸多肽的方法。为了证明这种方法在生物活性多肽中用二氨基戊二酸取代胱氨酸是有用的，我们构建了两个来自Sandostatin和TT-232的环状生长抑素类似物。硝基藜芦基类型的光解可裂解的胺衍生物用于UGI四组分缩合。由于二氨基戊二酸的新立体中心的消旋作用和异腈成分的消旋作用，四个非对映体多肽被高效液相色谱分离。通过手性气相色谱和对映体纯(2S.4S)-二氨基戊二酸的参比样品，可以方便而明确地指认环肽的立体化学结构。版权所有(C)2001欧洲多肽协会和John Wiley&Sons，Ltd.
A new synthesis of orthogonally protected diaminoglutaric acid containing peptides rising the Ugi four component condensation is presented. To demonstrate that this method is useful to replace cystine by diaminoglutaric acid in biologically interesting peptides, we built up two cyclic somatostatin analogues deriving from Sandostatin and from TT-232. A photolytically cleavable amine derivative of the nitroveratryl type is used for the Ugi four component condensation. Because of a racemic build up of the new stereocentre of the diaminoglutaric acid, and racemization of the isonitrile component, four diastercomeric peptides resulted that were separated by HPLC. The stereochemistry of the cyclopeptides could be easily and unambiguously assigned by chiral gas chromatography and a reference sample of enantiomerically pure (2S.4S)-diaminoglutaric acid. Copyright (C) 2001 European Peptide Society and John Wiley & Sons, Ltd.