SOLUTION-PHASE-PEPTIDE SYNTHESIS WITHOUT PURIFICATION OF COLUMN CHROMATOGRAPHY AND RECRYSTALLIZATION BY PROTECTING AMINO ACID ESTERS WITH PHOSPHINYL CHLORIDE

被引：3

作者：

An, Guanghui ^{[1
]}

Zhou, Wei ^{[2
]}

Xu, Xiaokang ^{[1
]}

Pan, Yi ^{[2
]}

Li, Guigen ^{[1
,2
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

[2] Nanjing Univ, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China

来源：

HETEROCYCLES | 2015年 / 90卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Group-Assisted Purification; GAP Chemistry; Peptide; Phosphinyl Chloride; N-PHOSPHONYL IMINES; OPIOID PEPTIDE; DESIGN; ENKEPHALINS; CHEMISTRY; STRATEGIES; BIPHALIN; BRAIN;

D O I：

10.3987/COM-14-S(K)99

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biphenyl phosphinyl chloride (Bpp-Cl) has been successfully applied for the amino acid GAP (Group-Assisted Purification) protection. The resulting N-protected amino acid esters have been readily converted into the corresponding amino acids and peptides through GAP operation. Biphalin, enkephalin derivatives and the fragments of surfaxin have also been synthesized via GAP work-up by avoiding column chromatography. The GAP protecting group (Bpp) can be recovered and can implement the former phosphonyl groups in peptide synthesis.

引用

页码：1405 / 1418

页数：14

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