α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base

被引：1

作者：

Sawamura, Jun ^{[1
]}

Ieiri, Daikan ^{[1
]}

Yazaki, Ryo ^{[1
]}

Ohshima, Takashi ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

PRECISION CHEMISTRY | 2023年 / 2卷 / 01期

基金：

日本科学技术振兴机构;

关键词：

alpha; beta-dehydroamino acid; peptide; proline; aldol condensation; glycine Schiff base; transimination; ALPHA-AMINO-ACIDS; PHASE-TRANSFER CATALYSIS; ROBUSTNESS SCREEN; PEPTIDE-SYNTHESIS; IMINE METATHESIS; EFFICIENT METHOD; TRANSIMINATION; ALDEHYDES; ESTERS; DERIVATIVES;

D O I：

10.1021/prechem.3c00048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general protocol for the synthesis of alpha,beta-dehydroamino acids and their peptides was developed. Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes. The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-free alpha,beta-dehydroamino esters. Peptide elongation of both the C- and N-terminals highlighted the usefulness of our present protocol.

引用

页码：14 / 20

页数：7

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