A new approach to the synthesis of di- and tripeptides with unnatural amino acids using organozinc chemistry

被引:14
作者
Dunn, MJ [1 ]
Jackson, RFW [1 ]
机构
[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4020(97)00879-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Di- and tripeptides which incorporate an iodoalanine unit at the C-terminus can be converted into the corresponding organozinc reagents upon treatment with activated zinc. These C-terminal di-and tripeptide organozinc reagents react with electrophiles either under palladium catalysis, or by prior transmetallation to a zinc/copper reagent, to give di-and tripeptides incorporating non-proteinogenic amino acids without loss of stereochemical purity. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:13905 / 13914
页数:10
相关论文
共 27 条
[1]   STEREOSPECIFIC SYNTHESIS OF CHLAMYDOCIN [J].
BALDWIN, JE ;
ADLINGTON, RM ;
GODFREY, CRA ;
PATEL, VK .
TETRAHEDRON, 1993, 49 (36) :7837-7856
[2]   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
[3]   PALLADIUM-CATALYZED REDUCTIVE DEPROTECTION OF ALLOC - TRANSPROTECTION AND PEPTIDE-BOND FORMATION [J].
BEUGELMANS, R ;
NEUVILLE, L ;
BOISCHOUSSY, M ;
CHASTANET, J ;
ZHU, JP .
TETRAHEDRON LETTERS, 1995, 36 (18) :3129-3132
[4]   PEPTIDE ENOLATES - C-ALKYLATION OF GLYCINE RESIDUES IN LINEAR TRIPEPTIDES, TETRAPEPTIDES, AND PENTAPEPTIDES VIA DILITHIUM AZADIENEDIOLATES [J].
BOSSLER, HG ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1994, 77 (04) :1124-1165
[5]   FREE-RADICAL ADDITION TO DIPEPTIDES AND TRIPEPTIDES CONTAINING DEHYDROALANINE RESIDUES [J].
CRICH, D ;
DAVIES, JW .
TETRAHEDRON, 1989, 45 (17) :5641-5654
[6]   PREPARATION AND REACTIVITY OF CHIRAL BETA-AMIDO-ALKYLZINC IODIDES AND RELATED CONFIGURATIONALLY STABLE ZINC ORGANOMETALLICS [J].
DUDDU, R ;
ECKHARDT, M ;
FURLONG, M ;
KNOESS, HP ;
BERGER, S ;
KNOCHEL, P .
TETRAHEDRON, 1994, 50 (08) :2415-2432
[7]   A NEW APPROACH TO THE SYNTHESIS OF DIPEPTIDES WITH UNNATURAL AMINO-ACIDS USING ORGANOZINC CHEMISTRY [J].
DUNN, MJ ;
GOMEZ, S ;
JACKSON, RFW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13) :1639-1640
[8]   SYNTHESIS OF ENANTIOMERICALLY PURE UNSATURATED ALPHA-AMINO-ACIDS USING SERINE-DERIVED ZINZ/COPPER REAGENTS [J].
DUNN, MJ ;
JACKSON, RFW ;
PIETRUSZKA, J ;
TURNER, D .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2210-2215
[9]  
FISCHER E, 1961, J BIOL CHEM, V1941, P137
[10]  
FRASER JL, 1995, SYNLETT, P819