Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids
Preparation and reactivity of aminoacyl pyroglutamates. Facile synthesis of 10-membered-ring cyclic dipeptides derived from 1,4-diaminobutyric and glutamic acids
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DOI：
10.1002/psc.611
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发表时间：
2005-03-01
影响因子：
2.1
通讯作者：
Ivanov, VT
中科院分区：
文献类型：
--
作者：
Chulin, AN;Rodionov, IL;Ivanov, VT
用RuO_4对含脯氨酸的二肽进行无差向异构化氧化，得到了含有焦谷氨酸残基的二肽Boc-Xaa-Pro-OBut。后者在Phl[OC（O）CF 3]（2）的诱导下发生氧化Hoffman重排反应，得到N-（氨酰基）-焦谷氨酸。这些衍生物在碱性条件下的行为进行了研究，并为两个这样的衍生物的氨酰基掺入反应观察到，生产否则难以获得的10元环双内酰胺衍生自1，4-二氨基丁酸和谷氨酸在可行的产率。版权所有（c）2004欧洲肽协会和约翰威利父子有限公司。
A number of protected proline-containing dipeptides Boc-Xaa-Pro-OBut were converted via epimerization-free oxidation with RuO4 to dipeptides with an internal pyroglutamic acid residue, Boc-Xaa-Glp-OBut. The latter were subjected to oxidative Hoffman-type rearrangement induced by Phl[OC(O)CF3](2) to give N-(aminoacyl)-pyroglutamates. The behavior of these derivatives under basic conditions was studied, and for two such a derivatives an aminoacyl incorporation reaction was observed, producing otherwise poorly accessible 10-membered-ring dilactams derived from 1,4-diaminobutyric and glutamic acids in practicable yields. Copyright (c) 2004 European Peptide Society and John Wiley & Sons, Ltd.