RESOLUTION AND REGIOSELECTIVE PROTECTION OF GLUTAMIC-ACID ANALOGS .1. RESOLUTION OF DIASTEREOMERIC ALPHA-BOROXAZOLIDONE DERIVATIVES

被引:23
作者
ACHER, F [1 ]
AZERAD, R [1 ]
机构
[1] UNIV PARIS 05,CHIM & BIOCHIM PHARMACOL & TOXICOL LAB,CNRS,UNITE ASSOCIEE 400,F-75270 PARIS 06,FRANCE
关键词
D O I
10.1016/0957-4166(94)80036-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diastereomeric alpha-boroxazolidone gamma-phenylethylamide (or gamma-phenylethanolamide) derivatives of 2-, 3- or 4-substituted glutamic acid analogues have been separated by silicagel chromatography, resulting, after deprotection, in a practical method for the resolution of most of these unnatural amino acids.
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收藏
页码:731 / 744
页数:14
相关论文
共 95 条
[1]  
ABRAHAM A, 1909, J MED CHEM, V34, P222
[2]  
ACHER F, 1991, INT J PEPT PROT RES, V37, P210
[3]   OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ASPARTIC AND GLUTAMIC-ACID THROUGH DILITHIUM ENOLATOCARBOXYLATES OF 2-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]ACETIC AND 3-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]PROPIONIC ACID, RESPECTIVELY [J].
AEBI, JD ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1985, 68 (06) :1507-1518
[4]   VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE [J].
ALTMANN, E ;
NEBEL, K ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1991, 74 (04) :800-806
[5]   CONFORMATIONAL STUDIES ON PEPTIDES CONTAINING ENANTIOMERIC ALPHA-METHYL ALPHA-AMINO-ACIDS .1. DIFFERENTIAL CONFORMATIONAL PROPERTIES OF (R)-2-METHYLASPARTIC AND (S)-2-METHYLASPARTIC ACID [J].
ALTMANN, KH ;
ALTMANN, E ;
MUTTER, M .
HELVETICA CHIMICA ACTA, 1992, 75 (04) :1198-1210
[6]   RESOLUTION OF ALPHA-METHYL AMINO ESTERS BY CHYMOTRYPSIN [J].
ANANTHARAMAIAH, GM ;
ROESKE, RW .
TETRAHEDRON LETTERS, 1982, 23 (33) :3335-3336
[7]   QUANTITATIVE REMOVAL OF A PENTADECAPEPTIDE ACTH FRAGMENT ANALOG FROM A MERRIFIELD RESIN USING AMMONIUM FORMATE CATALYTIC TRANSFER HYDROGENATION - SYNTHESIS OF [ASP25,ALA26,GLY27,GLN30]-ACTH-(25-39)-OH [J].
ANWER, MK ;
SPATOLA, AF ;
BOSSINGER, CD ;
FLANIGAN, E ;
LIU, RC ;
OLSEN, DB ;
STEVENSON, D .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3503-3507
[8]  
AZERAD R, 1988, CURRENT ADV VITAMIN, P17
[9]  
BAJGROWICZ JA, 1984, TETRAHEDRON LETT, V25, P2179
[10]   OPTICAL ENANTIOMORPHS OF ISOVALINE [J].
BAKER, CG ;
FU, SCJ ;
BIRNBAUM, SM ;
SOBER, HA ;
GREENSTEIN, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (18) :4701-4702