Cystine mimetics - solid phase lanthionine synthesis

被引:24
作者
Matteucci, M
Bhalay, G
Bradley, M [1 ]
机构
[1] Univ Southampton, Dept Chem, Combinatorial Ctr Excellence, Southampton SO17 1BJ, Hants, England
[2] Novartis Pharmaceut, Horsham RH12 5AB, W Sussex, England
基金
英国工程与自然科学研究理事会;
关键词
solid phase synthesis; lanthionine; dehydro peptides; lantibiotics;
D O I
10.1016/j.tetlet.2003.12.074
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total solid phase synthesis of an analogue of the B ring of nisin was achieved, in a biomimetic fashion, via the solid phase diastereoselective cyclisation of a dehydrothiol-containing peptide. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1399 / 1401
页数:3
相关论文
共 30 条
[1]  
Burrage S, 2000, CHEM-EUR J, V6, P1455, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1455::AID-CHEM1455>3.3.CO
[2]  
2-D
[3]   NEW DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED MESO-LANTHIONINE WITH DISCRIMINATION OF THE CHIRAL CENTERS [J].
CAVELIERFRONTIN, F ;
DAUNIS, J ;
JACQUIER, R .
TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :85-94
[4]   Cyclic dipeptides.: 3.: Synthesis of methyl (R)-6-[(tert-butoxycarbonyl)amino]-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylate and its hexahydro analogues:: Elaboration of a novel dual ACE NEP inhibitor [J].
Crescenza, A ;
Botta, M ;
Corelli, F ;
Santini, A ;
Tafi, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3019-3025
[5]   Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives [J].
Dugave, C ;
Menez, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1453-1465
[6]   SYNTHETIC STUDY ON PEPTIDE ANTIBIOTIC NISIN .5. TOTAL SYNTHESIS OF NISIN [J].
FUKASE, K ;
KITAZAWA, M ;
SANO, A ;
SHIMBO, K ;
HORIMOTO, S ;
FUJITA, H ;
KUBO, A ;
WAKAMIYA, T ;
SHIBA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (08) :2227-2240
[7]   A facile method for the direct synthesis of lanthionine containing cyclic peptides [J].
Galande, AK ;
Spatola, AF .
LETTERS IN PEPTIDE SCIENCE, 2001, 8 (3-5) :247-251
[8]  
Goodman M, 2001, BIOPOLYMERS, V60, P229, DOI 10.1002/1097-0282(2001)60:3<229::AID-BIP10034>3.0.CO
[9]  
2-P
[10]   Peptidomimetic building blocks for drug discovery: An overview [J].
Goodman, M ;
Shao, H .
PURE AND APPLIED CHEMISTRY, 1996, 68 (06) :1303-1308