CHIRAL HPLC-CD STUDIES OF THE ANTITUBERCULOSIS DRUG (+)-ETHAMBUTOL

被引：6

作者：

BLESSINGTON, B ^{[1
]}

BEIRAGHI, A ^{[1
]}

LO, TW ^{[1
]}

DRAKE, A ^{[1
]}

JONAS, G ^{[1
]}

机构：

[1] UNIV LONDON BIRKBECK COLL,SERC CD SERV,LONDON WC1E 7HX,ENGLAND

来源：

CHIRALITY | 1992年 / 4卷 / 04期

关键词：

CIRCULAR DICHROISM; EXCITON COUPLING; DERIVATIZATION; TETRABENZOYLETHAMBUTOL; DIBENZOYL-2-AMINOBUTAN-1-OL; ABSOLUTE STEREOCHEMISTRY; PIRKLE COLUMN;

D O I：

10.1002/chir.530040405

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Long standing errors in major pharmacopoeiae (BP,USP, and Eu.Ph.) concerning the absolute stereochemistry of the widely used antituberculosis drug (+)-ethambutol have been clarified by unambiguous synthesis and chiral HPLC. on a Pirkle, covalent D-phenylglycine column of perbenzoyl derivatives of each stereomer; the enantiomeric (-)-(R,R) and (+)-(S,S)-ethambutols together with the optically inactive (meso)-(R,S)-ethambutol. This paper describes how circular dichroism (CD) alone and combined with HPLC is used to demonstrate this chiral separation and also to confirm the absolute stereochemistry of each stereomer of ethambutol and its synthetic precursor 2-aminobutan-1-ol from studies of "exciton coupling." The strengths and weaknesses of these chiral techniques are discussed.

引用

页码：227 / 229

页数：3