Efficient protocols for the synthesis of enantiopure γ-amino acids with proteinogenic side chains
Efficient protocols for the synthesis of enantiopure γ-amino acids with proteinogenic side chains
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DOI：
10.1002/psc.458
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发表时间：
2003-05-01
影响因子：
2.1
通讯作者：
Kokotos, G
中科院分区：
文献类型：
--
作者：
Loukas, V;Noula, C;Kokotos, G
以相应的天然α-氨基酸为起始原料，研究了含蛋白侧链的对映体伽马取代的伽马氨基酸的合成。以相应的氨基醇为原料，在AcNH-TEMPO存在下，用NaOCl氧化得到含不同保护基团的N-保护氨基醛，再与甲基、苄基和叔丁基亚磷酰基乙酸酯直接反应生成α，β-不饱和伽马氨基酯。双键的同时加氢和去掉苄基或苄氧基羰基可以高产率地得到N-或C-保护的伽马氨基酸。通过Mosher酰胺的H-1核磁共振分析和手性高效液相色谱分析研究了产物的对映体纯度。版权所有(C)2003欧洲肽协会和John Wiley Sons，Ltd.
The synthesis of enantiopure gamma-substituted gamma-amino acids with proteinogenic side chains, starting from the corresponding natural alpha-amino acids, was studied. N-Protected amino aldehydes containing various protective groups were prepared from the corresponding amino alcohols by oxidation with NaOCl in the presence of AcNH-TEMPO and directly reacted with methyl, benzyl and tert-butyl phosphoranylidene acetate to produce alpha, beta-unsaturated gamma-amino esters. Simultaneous hydrogenation of the double bond and removal of either the benzyl or benzyloxycarbonyl group led to N- or C-protected gamma-amino acids in high yield. The enantiomeric purity was studied by H-1 NMR analysis of Mosher amides and chiral HPLC analysis. Copyright (C) 2003 European Peptide Society and John Wiley Sons, Ltd.