Convenient Preparations of Chiral N, N'-Ethylene-Bridged Dipeptides and Their Uses as Units of Pseudopeptides
Convenient Preparations of Chiral N, N'-Ethylene-Bridged Dipeptides and Their Uses as Units of Pseudopeptides
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手性N,N-亚乙基桥二肽的简便制备及其作为伪肽单元的用途
DOI：
10.5059/yukigoseikyokaishi.54.94
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发表时间：
1996
影响因子：
0.2
通讯作者：
T. Yamashita
中科院分区：
文献类型：
--
作者：
Y. Kojima;T. Yamashita
一些工作者合成了手性和非手性的N，N '-亚乙基桥连二肽（哌嗪-2-酮衍生物），并将其主要用作具有生物活性的假肽单元，如脑啡肽类似物，因为这些结构受限的亲脂性二肽赋予生物活性肽抗酶水解的特性。但是，它们的合成方法存在一些问题（非立体选择性、多步骤、工艺麻烦、试剂昂贵等）。因此，我们开发了更方便的方法来制备N，N '-亚乙基桥连二肽。本文报道了四种以不同的（R）或（S）-α-氨基酸为原料合成手性N，N ′-亚乙基桥连二肽的方法。此外，还介绍和讨论了大环假肽的结构和功能（（R）-和（S）-铵盐的对映选择性包合和转运，金属离子的络合）以及以这些二肽为单元的线性假肽的脑啡肽和皮吗啡样生物活性的一系列研究。本文还介绍了由大环假肽经BH_3还原得到的大环多胺的合成及其金属配离子的结构。
Several workers have synthesized chiral and achiral N, N'-ethylene-bridged dipeptides (piperazin-2-one derivatives), and used them mainly as units of biologically active pseudopeptides such i : as enkephalin analogs because these structurally constrained and lipophilic dipeptides afford the character resisting enzymatic hydrolysis to biologically active peptides. However, their synthetic methods have some problems (nonstereoselective, multi-steps, troublesome techniques, expensive reagents etc.) Therefore; we have developed more convenient procedures for preparing N, N'-ethylene-bridged dipeptides. This article reports four kinds of synthetic methods of chiral N, N'-ethylene-bridged dipeptides, in which various (R) or (S) -α-amino acids are used as starting materials. Moreover, a series of studies on the structures and the functionalities (enantioselective inclusion and transport of (R) - and (S) -ammonium salts, complexing of metal ions) of macrocyclic pseudopeptides and on the enkephalin- and dermorphin-like biological activities of linear pseudopeptides containing these dipeptides as their units are introduced and discussed. Also, the synthesis of a macrocyclic polyamine obtained by the BH3 reduction of macrocyclic pseudopeptide and the structure of its metal complex ion are described.