An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate "Na2CO3/n-Al2O3'

被引：1

作者：

Hashimoto, Chikao ^{[1
]}

Sugimoto, Kazuhiro ^{[2
]}

Takahashi, Youhei ^{[2
]}

Kodomari, Mitsuo ^{[2
]}

机构：

[1] Jikei Univ, Sch Med, Dept Chem, Choufu, Tokyo 1828570, Japan

[2] Shibaura Inst Technol, Dept Biosci & Engn, Minuma Ku, Saitama 3378570, Japan

来源：

JOURNAL OF PEPTIDE SCIENCE | 2013年 / 19卷 / 10期

关键词：

neutral alumina-supported sodium carbonate; solid base; phenacyl ester; peptide synthesis; amine; AMINO-ACIDS; PEPTIDES;

D O I：

10.1002/psc.2544

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In the synthesis of dipeptides (Boc-AA(1)-AA(2)-OPac: AA(1) and AA(2) represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA center dot H-AA(2)-OPac) into the corresponding free amino component (H-AA(2)-OPac) were examined. The synthesis of a dipeptide (Boc-Ala-Gly-OPac) using amines for the conversion afforded an unsatisfactory yield with by-products. On the other hand, the use of neutral alumina-supported Na2CO3 (Na2CO3/n-Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by-products. The application of Na2CO3/n-Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. Copyright (c) 2013 European Peptide Society and John Wiley & Sons, Ltd.

引用

页码：659 / 662

页数：4

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