AMINO-ACIDS AND PEPTIDES .17. SYNTHESIS OF CYCLO-[(O-T-BUTYL)-L-SERYL-BETA-ALANYL-GLYCYL-(O-METHYL)-L-BETA-ASPARTYL], AND OBSERVATIONS ON REARRANGEMENT OF BETA-ASPARTYL PEPTIDE ESTERS
AMINO-ACIDS AND PEPTIDES .17. SYNTHESIS OF CYCLO-[(O-T-BUTYL)-L-SERYL-BETA-ALANYL-GLYCYL-(O-METHYL)-L-BETA-ASPARTYL], AND OBSERVATIONS ON REARRANGEMENT OF BETA-ASPARTYL PEPTIDE ESTERS
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DOI：
10.1039/p19760002014
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发表时间：
1976-01-01
期刊：
影响因子：
--
通讯作者：
HASSALL, CH
中科院分区：
文献类型：
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作者：
HANDA, BK;HASSALL, CH
通过环化相应的直链四肽对硝基苯酯合成标题14元环系统。当尝试用末端β-丙氨酸和甘氨酸残基使相关四肽闭环时，没有形成环肽；天冬氨酰残基非常容易地从β-重排至α-。含有β-天冬氨酰残基的几种肽的合成证实，序列O-甲基-L-β-天冬氨酰-(O-叔丁基)-L-丝氨酰-β-丙氨酰特别有利于这种重排。
The title 14-membered ring system as synthesized by cyclization of the corresponding linear tetrapeptide p-nitrophenyl ester. When ring closure of the related tetrapeptide with terminal .beta.-alanine and glycine residues was attempted, no cyclic peptide was formed; the aspartyl residue rearranged remarkably readily from .beta.- to .alpha.-. The synthesis of several peptides containing .beta.-aspartyl residues established that the sequence O-methyl-L-.beta.-aspartyl-(O-t[tert]-butyl)-L-seryl-.beta.-alanyl particularly favored this rearrangement.