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

被引：12

作者：

Davies, DE

Doyle, PM

Farrant, RD

Hill, RD

Hitchcock, PB

Sanderson, PN

Young, DW ^{[1
]}

机构：

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

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

[3] BioFocus Discovery PLC, Sittingbourne Res Ctr, Sittingbourne ME9 8AZ, Kent, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 49期

关键词：

beta-turn; protein mimetic; amino acid; bicyclic lactam;

D O I：

10.1016/j.tetlet.2003.09.170

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 4, designed as an external turn constraint, was synthesised by a new stereoselective route involving Eschenmoser condensation. Calculated preferred conformations compare well with the preferred solid state conformation. obtained by X-ray crystallography. The lactam 4 was not a turn mimic in its own right but Could be used as an external constraint to prepare the cyclic peptide 29 containing the integrin recognition motif GLDV. High-resolution NMR measurements were consistent with this compound having a single backbone conformation. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8887 / 8891

页数：5

共 18 条

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