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Chiral hplc-cd studies of the antituberculosis drug (+)-ethambutol

✍ Scribed by B. Blessington; A. Beiraghi; T.W. Lo; A. Drake; G. Jonas

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
204 KB
Volume
4
Category
Article
ISSN
0899-0042

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✦ Synopsis

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-1-01 from studies of "exciton coupling." The strengths and weaknesses of these chiral techniques are discussed.

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