Amino Acid-Protecting Groups

被引：676

作者：

Isidro-Llobet, Albert ^{[1
]}

Alvarez, Mercedes ^{[1
,2
,3
]}

Albericio, Fernando ^{[1
,2
,4
]}

机构：

[1] Inst Res Biomed, Barcelona 08028, Spain

[2] Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona 08028, Spain

[3] Univ Barcelona, Organ Chem Lab, Fac Pharm, E-08028 Barcelona, Spain

[4] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

来源：

CHEMICAL REVIEWS | 2009年 / 109卷 / 06期

关键词：

SOLID-PHASE SYNTHESIS; SIDE-CHAIN PROTECTION; P-NITROBENZYLOXYCARBONYL PNZ; N-ALPHA-FMOC; NIM-TOSYLHISTIDINE DERIVATIVES; DISULFIDE BOND FORMATION; ESTERS CAM-ESTERS; PEPTIDE-SYNTHESIS; TERT-BUTYL; TRIFLUOROACETIC-ACID;

D O I：

10.1021/cr800323s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted by a team of researchers to investigate amino acid-protecting groups. A number of methododologies were introduced to demonstrate the protection of these groups. The protecting groups were classified according to a number of criteria, such as the most used groups in a Boc/Bn strategy, the most used in a Fmoc/tBu strategy, decreased order of liability, and the latest described groups. It was demonstrated that different methodologies were used to protect a large number of α-amino-protecting groups. Most of the protection methodologies were based on the reaction of the free amino acids with a haloformate or dicarbonate of the protecting group under Schotten Baumann conditions. A number of methodologies involving a carboxylic acid-protecting group were used in the investigations to overcome the problem of the presence of interfering α-carboxylic acid.

引用

页码：2455 / 2504

页数：50

共 471 条

[1] Incorporation of pseudoproline derivatives allows the facile synthesis of human IAPP, a highly amyloidogenic and aggregation-prone polypeptide [J].