EUROPIUM (S,S)-ETHYLENEDIAMINE-N,N'-DISUCCINATE AS A CHIRAL LANTHANIDE SHIFT-REAGENT FOR AQUEOUS-SOLUTIONS

被引:24
作者
KIDO, J
OKAMOTO, Y
BRITTAIN, HG
机构
[1] BRISTOL MYERS SQUIBB CO,PHARMACEUT RES INST,POB 191,NEW BRUNSWICK,NJ 08903
[2] POLYTECH INST NEW YORK,DEPT CHEM,333 JAY ST,BROOKLYN,NY 11201
[3] POLYTECH INST NEW YORK,POLYMER RES INST,BROOKLYN,NY 11201
关键词
D O I
10.1021/jo00004a014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound has been utilized for H-1 NMR spectral resolution of enantiomeric amino acids in aqueous solutions. For the alpha-protons of D,L-phenylglycine, an enantiomeric shift difference, DELTA-DELTA-delta = 0.4 ppm, was observed at an Eu(EDDS):substrate ratio of 0.3. Association constants between Eu(EDDS) and D,L-phenylglycine were found to be different for each isomer, K(L) = 3.7 and K(D) = 6.1. Spectral resolution of other amino acids including alanine, serine, threonine, and phenylalanine was also achieved.
引用
收藏
页码:1412 / 1415
页数:4
相关论文
共 15 条
[1]  
BRITTAIN HG, IN PRESS J COORD CHE
[2]   DIRECT DETERMINATION OF ENANTIOMERIC COMPOSITIONS WITH OPTICALLY-ACTIVE NUCLEAR MAGNETIC-RESONANCE LANTHANIDE SHIFT-REAGENTS [J].
GOERING, HL ;
EIKENBER.JN ;
KOERMER, GS ;
LATTIMER, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) :1493-1501
[3]   THE EUROPIUM(III) (R)-PROPYLENEDIAMINETETRA-ACETATE ION - A PROMISING CHIRAL SHIFT-REAGENT FOR H-1-NMR SPECTROSCOPY IN AQUEOUS-SOLUTION [J].
KABUTO, K ;
SASAKI, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (05) :316-318
[4]  
KELTY SA, 1985, THESIS SETON HALL U
[5]   A NEW CHIRAL SHIFT-REAGENT FOR AQUEOUS-SOLUTIONS - EU[(S,S)-ETHYLENEDIAMINE-N,N'-DISUCCINATE], EU(EDDS) [J].
KIDO, J ;
OKAMOTO, Y ;
BRITTAIN, HG .
JOURNAL OF COORDINATION CHEMISTRY, 1990, 21 (02) :107-110
[6]  
MAJOR J, 1966, CHEM ZVESTI, V20, P414
[7]  
Martell A. E., 1974, CRITICAL STABILITY C, V1
[8]   DETERMINATION OF ENANTIOMERIC PURITY USING CHIRAL LANTHANIDE SHIFT-REAGENTS [J].
MCCREARY, MD ;
LEWIS, DW ;
WERNICK, DL ;
WHITESID.GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1038-1054
[9]   STEREOSPECIFIC LIGANDS AND THEIR COMPLEXES .I. A COBALT(3)COMPLEX OF ETHYLENEDIAMINEDISUCCINIC ACID [J].
NEAL, JA ;
ROSE, NJ .
INORGANIC CHEMISTRY, 1968, 7 (11) :2405-&
[10]   LANTHANIDE(III) SALTS OF (S)-CARBOXYMETHYLOXYSUCCINIC ACID - CHIRAL LANTHANIDE SHIFT-REAGENTS FOR AQUEOUS-SOLUTION [J].
PETERS, JA ;
VIJVERBERG, CAM ;
KIEBOOM, APG ;
VANBEKKUM, H .
TETRAHEDRON LETTERS, 1983, 24 (30) :3141-3144