PEPTIDE-SYNTHESIS - SYNTHESIS OF THE CYSTEINE-CONTAINING PEPTIDES OF BIOLOGICAL AND PHARMACEUTICAL INTEREST, ALPHA-H-ANF AND H-BIG ENDOTHELIN

被引：13

作者：

RAMAGE, R

STEWART, ASJ

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930001947

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The biologically important vasoactive peptides, alpha-h-atrial natriuretic factor (ANF) and h-Big endothelin (Big ET) have been synthesised using the solid-phase Fmoc strategy with reference to the choice of protecting group for cysteine residues. Selective disulfide bond formation was seen to be problematical in the synthesis of Big ET but use of the acetamidomethyl (Acm) group, removal with the silver ions and oxidation using the mixed disulfide method proved successful.

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页码：1947 / 1952

页数：6

相关论文

共 25 条

[1]

AMIARD G, 1956, B SOC CHIM FR, P698

[2] PEPTIDE-SYNTHESIS .7. SOLID-PHASE SYNTHESIS OF CONOTOXIN-G1 [J].

ATHERTON, E ;

SHEPPARD, RC ;

WARD, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (10) :2065-2073

[3]

CASARETTO R, 1990, PEPTIDES, P181

[4]

DECASTIGLIONE R, 1989, PEPTIDES, P402

[5] ENDOTHELIN - A NEW CHALLENGE [J].

DOHERTY, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (09) :1493-1508

[6] ON THE USE OF S-TERT-BUTYLSULPHENYL GROUP FOR PROTECTION OF CYSTEINE IN SOLID-PHASE PEPTIDE-SYNTHESIS USING FMOC-AMINO ACIDS [J].

ERITJA, R ;

ZIEHLERMARTIN, JP ;

WALKER, PA ;

LEE, TD ;

LEGESSE, K ;

ALBERICIO, F ;

KAPLAN, BE .

TETRAHEDRON, 1987, 43 (12) :2675-2680

[7] SILVER TRIFLUOROMETHANESULFONATE AS AN S-DEPROTECTING REAGENT FOR THE SYNTHESIS OF CYSTINE PEPTIDES [J].

FUJII, N ;

OTAKA, A ;

WATANABE, T ;

OKAMACHI, A ;

TAMAMURA, H ;

YAJIMA, H ;

INAGAKI, Y ;

NOMIZU, M ;

ASANO, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) :283-284

[8] PEPTIDES .46. STUDIES IN THE SYNTHESIS OF AN ANALOG OF HEN EGG-WHITE LYSOZYME [J].

GALPIN, IJ ;

HANCOCK, FE ;

HANDA, BK ;

JACKSON, AG ;

KENNER, GW ;

MCDOWELL, P ;

NOBLE, P ;

RAMAGE, R .

TETRAHEDRON, 1981, 37 (17) :3043-3050

[9] 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

[10]

GREEN J, 1987, THESIS U EDINBURGH