Synthesis of an external beta-turn based on the GLDV motif of cell adhesion proteins

被引：7

作者：

Davies, DE

Doyle, PM

Hill, RD

Young, DW ^{[1
]}

机构：

[1] Univ Sussex, Sussex Ctr Biomol Design & Drug Dev, Dept Chem, Brighton BN1 9QJ, E Sussex, England

[2] Biofocus Discovery Ltd, Saffron Walden CB10 1XL, Essex, England

[3] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2005年 / 61卷 / 01期

关键词：

bicyclic lactam; integrin; Eschenmoser olefination;

D O I：

10.1016/j.tet.2004.09.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (3S,6S, 10S)-7/5 bicyclic lactam 8, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. The cyclic peptide 35 containing the integrin recognition motif GLDV added across the amino and carboxyl groups of the lactam external constraint 8 was prepared. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：301 / 312

页数：12

相关论文

共 24 条

[1]

ANDERSEN TP, 1986, LIEBIGS ANN CHEM, P269

[2] Potent integrin antagonists from a small library of RGD-including cyclic pseudopeptides [J].

Belvisi, L ;

Bernardi, A ;

Checchia, A ;

Manzoni, L ;

Potenza, D ;

Scolastico, C ;

Castorina, M ;

Cupelli, A ;

Giannini, G ;

Carminati, P ;

Pisano, C .

ORGANIC LETTERS, 2001, 3 (07) :1001-1004

[3]

BERRY JM, 2004, TETRAHEDRON, V60

[4] ELECTROCHEMICAL CYCLIZATION OF DIPEPTIDES TOWARD NOVEL BICYCLIC, REVERSE-TURN PEPTIDOMIMETICS .1. SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 7,5-BICYCLIC SYSTEMS [J].

CORNILLE, F ;

SLOMCZYNSKA, U ;

SMYTHE, ML ;

BEUSEN, DD ;

MOELLER, KD ;

MARSHALL, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :909-917

[5] Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins [J].

Davies, DE ;

Doyle, PM ;

Farrant, RD ;

Hill, RD ;

Hitchcock, PB ;

Sanderson, PN ;

Young, DW .

TETRAHEDRON LETTERS, 2003, 44 (49) :8887-8891

[6]

Doyle PM, 1996, INT J PEPT PROT RES, V47, P427

[7] SYNTHESIS OF L-SERINE STEREOSPECIFICALLY LABELED AT C-3 WITH DEUTERIUM [J].

GANI, D ;

YOUNG, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2393-2398

[8]

Haubner R., 1997, ANGEW CHEM INT EDIT, V36, P1374

[9] 1-HYDROXY-3-AMINO-2-PIPERIDONE (DELTA-N-HYDROXYCYCLOORNITHINE) DERIVATIVES - KEY INTERMEDIATES FOR THE SYNTHESIS OF HYDROXAMATE-BASED SIDEROPHORES [J].

KOLASA, T ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1711-1721

[10] SYNTHESIS OF A BICYCLIC DIPEPTIDE WITH THE SHAPE OF BETA-TURN CENTRAL PART [J].

NAGAI, U ;

SATO, K .

TETRAHEDRON LETTERS, 1985, 26 (05) :647-650