AN ACID LABILE ARGININE DERIVATIVE FOR PEPTIDE-SYNTHESIS - N(G)-2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULFONYL-L-ARGININE

被引：53

作者：

RAMAGE, R

GREEN, J

BLAKE, AJ

机构：

[1] Department of Chemistry, University of Edinburgh, Edinburgh, EH9 3JJ, West Mains Road

来源：

TETRAHEDRON | 1991年 / 47卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(01)86564-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A trifluoroacetic acid (TFA) labile protecting group for the guanidine side chain function of arginine has been developed. N(G)-(2,2,5,7,8-Pentamethylchroman-6-sulphonyl-L-arginine is cleaved rapidly in TFA or 50% TFA in dichloromethane at room temperature. The preparations of Fmoc.Arg(Pmc).OH and Bnpeoc.Arg(Pmc).OH are described.

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页码：6353 / 6370

页数：18

相关论文

共 27 条

[1] PEPTIDE-SYNTHESIS .2. PROCEDURES FOR SOLID-PHASE SYNTHESIS USING N-ALPHA-FLUORENYLMETHOXYCARBONYLAMINO-ACIDS ON POLYAMIDE SUPPORTS - SYNTHESIS OF SUBSTANCE-P AND OF ACYL CARRIER PROTEIN 65-74 DECAPEPTIDE [J].

ATHERTON, E ;

LOGAN, CJ ;

SHEPPARD, RC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :538-546

[2]

ATHERTON E, 1987, PEPTIDES ANAL SYNTHE, V9, P1

[3] ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[4] 9-FLUORENYLMETHOXYCARBONYL FUNCTION, A NEW BASE-SENSITIVE AMINO-PROTECTING GROUP [J].

CARPINO, LA ;

HAN, GY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) :5748-&

[5] Reduction of aryl-sulphamide by hydrogen iodide. [J].

Fischer, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1915, 48 :93-102

[6]

FUJINO M, 1981, CHEM PHARM BULL, V29, P2825

[7]

GOULD RO, 1985, CALC PROGRAM MOL GEO

[8] APPLICATION OF THE NG-(2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULPHONYL) DERIVATIVE OF FMOC-ARGININE TO PEPTIDE-SYNTHESIS [J].

GREEN, J ;

OGUNJOBI, OM ;

RAMAGE, R ;

STEWART, ASJ ;

MCCURDY, S ;

NOBLE, R .

TETRAHEDRON LETTERS, 1988, 29 (34) :4341-4344

[9] THE GX CRYSTALLOGRAPHIC PROGRAM SYSTEM [J].

MALLINSON, PR ;

MUIR, KW .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1985, 18 (FEB) :51-53

[10] SOLID PHASE PEPTIDE SYNTHESIS .1. SYNTHESIS OF A TETRAPEPTIDE [J].

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2149-&