Synthesis of a cyclic-thioether peptide which binds anti-cardiolipin antibodies

被引：13

作者：

Jones, DS ^{[1
]}

Gamino, CA ^{[1
]}

Randow, ME ^{[1
]}

Victoria, EJ ^{[1
]}

Yu, L ^{[1
]}

Coutts, SM ^{[1
]}

机构：

[1] La Jolla Pharmaceut Co, San Diego, CA 92121 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(98)01292-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thioether cyclized peptide analogue, 1, was synthesized using solid phase FMOC chemistry on HMPB-MBHA resin. alpha-Methylproline was introduced as an FMOC-alanyl-alpha-methylproline dipeptide, and the thioether was incorporated as FMOC-protected thioether tetrapeptide intermediate, 8. Compound 1 has been shown to bind anti-cardiolipin antibodies. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6107 / 6110

页数：4

相关论文

共 13 条

[1] MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1988, 44 (17) :5479-5486

[2] CONJUGATES OF DOUBLE-STRANDED OLIGONUCLEOTIDES WITH POLY(ETHYLENE GLYCOL) AND KEYHOLE LIMPET HEMOCYANIN - A MODEL FOR TREATING SYSTEMIC LUPUS-ERYTHEMATOSUS [J].

JONES, DS ;

HACHMANN, JP ;

OSGOOD, SA ;

HAYAG, MS ;

BARSTAD, PA ;

IVERSON, GM ;

COUTTS, SM .

BIOCONJUGATE CHEMISTRY, 1994, 5 (05) :390-399

[3] IMMUNOSPECIFIC REDUCTION OF ANTIOLIGONUCLEOTIDE ANTIBODY-FORMING-CELLS WITH A TETRAKIS-OLIGONUCLEOTIDE CONJUGATE (LJP-394), A THERAPEUTIC CANDIDATE FOR THE TREATMENT OF LUPUS NEPHRITIS [J].

JONES, DS ;

BARSTAD, PA ;

FEILD, MJ ;

HACHMANN, JP ;

HAYAG, MS ;

HILL, KW ;

IVERSON, GM ;

LIVINGSTON, DA ;

PALANKI, MS ;

TIBBETTS, AR ;

YU, L ;

COUTTS, SM .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (12) :2138-2144

[4] STRUCTURE-BASED DESIGN OF HIGH-AFFINITY STREPTAVIDIN BINDING CYCLIC PEPTIDE LIGANDS CONTAINING THIOETHER CROSS-LINKS [J].

KATZ, BA ;

JOHNSON, CR ;

CASS, RT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (33) :8541-8547

[5] SYNTHESIS OF CYCLIC-PEPTIDES BY SOLID-PHASE METHODOLOGY [J].

LEBL, M ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1984, 25 (20) :2067-2068

[6] AN ALTERNATIVE SOLID-PHASE APPROACH TO C-1-OXYTOCIN [J].

MAYER, JP ;

HEIL, JR ;

ZHANG, JG ;

MUNSON, MC .

TETRAHEDRON LETTERS, 1995, 36 (41) :7387-7390

[7] THE SYNTHESIS OF CYCLIC-PEPTIDES USING FMOC SOLID-PHASE CHEMISTRY AND THE LINKAGE AGENT 4-(4-HYDROXYMETHYL-3-METHOXYPHENOXY)-BUTYRIC ACID [J].

MCMURRAY, JS ;

LEWIS, CA .

TETRAHEDRON LETTERS, 1993, 34 (50) :8059-8062

[8]

MIHARA H, 1995, TETRAHEDRON LETT, V36, P4837

[9] ALKYLATION OF AMINO-ACIDS WITHOUT LOSS OF THE OPTICAL-ACTIVITY - PREPARATION OF ALPHA-SUBSTITUTED PROLINE DERIVATIVES - A CASE OF SELF-REPRODUCTION OF CHIRALITY [J].

SEEBACH, D ;

BOES, M ;

NAEF, R ;

SCHWEIZER, WB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (16) :5390-5398

[10]

SEM DS, UNPUB