SAFETY-CATCH ANCHORING LINKAGE FOR SYNTHESIS OF PEPTIDE AMIDES BY BOC FMOC STRATEGY

被引：61

作者：

PATEK, M ^{[1
]}

LEBL, M ^{[1
]}

机构：

[1] CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECHOSLOVAKIA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)79406-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Methoxy-4,4'-bis(methylthio)benzhydrylamine (10) and the corresponding disulfoxide were prepared and tested as a model amide protecting groups for their stability toward acidic conditions. Subsequently, the novel 4-[4,4'-bis(methylsulfinyl)-2-oxy-(9-fluorenylmethyloxycarbonyl) benzhydrylamino]butanoic acid (SCAL) handle (9) has been prepared and applied to solid-phase peptide synthesis of C-terminal peptide amide using both 9-fluorenylmethyloxycarbonyl (Fmoc) and tert-butyloxycarbonyl (Boc) groups for N-alpha-amino protection.

引用

页码：3891 / 3894

页数：4

共 11 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]

ALBERICIO F, 1987, INT J PEPT PROT RES, V30, P206

[3] NEW AMINO PROTECTING GROUP REMOVABLE BY REDUCTION - CHEMISTRY OF DITHIASUCCINOYL (DTS) FUNCTION [J].

BARANY, G ;

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) :7363-7365

[4] SOLID-PHASE PEPTIDE-SYNTHESIS UTILIZING 9-FLUORENYLMETHOXYCARBONYL AMINO-ACIDS [J].

FIELDS, GB ;

NOBLE, RL .

INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (03) :161-214

[5]

FUJII N, 1987, CHEM PHARM BULL, V35, P3880

[6]

GAEHDE SA, 1981, INT J PEPT PROT RES, V18, P451

[7] A NEW CLASS OF AMINO PROTECTING GROUP REMOVABLE BY REDUCTIVE ACIDOLYSIS - THE 4-METHYLSULPHINYLBENZYLOXYCARBONYL (MSZ) GROUP [J].

KISO, Y ;

KIMURA, T ;

YOSHIDA, M ;

SHIMOKURA, M ;

AKAJI, K ;

MIMOTO, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1511-1513

[8] FLUORIDE-ION PROMOTED SYNTHESIS OF ALKYL PHENYL ETHERS [J].

MILLER, JM ;

SO, KH ;

CLARK, JH .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (14) :1887-1889

[9] A SAFETY CATCH TYPE OF AMIDE PROTECTING GROUP [J].

PATEK, M ;

LEBL, M .

TETRAHEDRON LETTERS, 1990, 31 (36) :5209-5212

[10]

PATEK M, IN PRESS COLLECT CZE

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