New stable backbone linker resins for solid-phase peptide synthesis

被引：23

作者：

Gu, WX

Silverman, RB

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[2] Northwestern Univ, Drug Discovery Program, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 04期

关键词：

D O I：

10.1021/ol027212g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Two new 4-methoxybenzaldehyde backbone linker resins were developed for the solid-phase synthesis of peptides. The linkers are very stable during the cleavage of common protecting groups for amines (Fmoc, Boc) and carboxylic acids (Me, All, tBu) in peptide synthesis. Cleavage from the resin with refluxing TFA is sufficiently mild for peptides; containing polar and nonpolar amino acids.

引用

收藏

页码：415 / 418

页数：4

相关论文

共 21 条

[1] PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].

ALBERICIO, F ;

KNEIBCORDONIER, N ;

BIANCALANA, S ;

GERA, L ;

MASADA, RI ;

HUDSON, D ;

BARANY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743

[2] Backbone amide linker (BAL) strategy for Nα-9-fluorenylmethoxycarbonyl (Fmoc) solid-phase synthesis of unprotected peptide p-nitroanilides and thioesters [J].

Alsina, J ;

Yokum, TS ;

Albericio, F ;

Barany, G .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8761-8769

[3] Solid-supported synthesis of imidazoles: A strategy for direct resin-attachment to the imidazole core [J].

Bilodeau, MT ;

Cunningham, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2800-2801

[4] Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality [J].

Boojamra, CG ;

Burow, KM ;

Thompson, LA ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1240-1256

[5] AN EXPEDIENT AND HIGH-YIELDING METHOD FOR THE SOLID-PHASE SYNTHESIS OF DIVERSE 1,4-BENZODIAZEPINE-2,5-DIONES [J].

BOOJAMRA, CG ;

BUROW, KM ;

ELLMAN, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5742-5743

[6] A backbone linker for BOC-based peptide synthesis and on-resin cyclization: Synthesis of stylostatin 1 [J].

Bourne, GT ;

Meutermans, WDF ;

Alewood, PF ;

McGeary, RP ;

Scanlon, M ;

Watson, AA ;

Smythe, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3095-3101

[7] A simple amide protecting group: synthesis of oligoamides of Nylon 6 [J].

Brooke, GM ;

Mohammed, S ;

Whiting, MC .

CHEMICAL COMMUNICATIONS, 1997, (16) :1511-1512

[8] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].

CARPINO, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398

[9] AMEBA: An acid sensitive aldehyde resin for solid phase synthesis [J].

Fivush, AM ;

Willson, TM .

TETRAHEDRON LETTERS, 1997, 38 (41) :7151-7154

[10]

Fresno M., 1998, TETRAHEDRON LETT, V39, P2639