ISSN:
0899-0042
Keywords:
circular dichroism
;
exciton coupling
;
derivatisation
;
tetrabenzoylethambutol
;
dibenzoyl-2-aminobutan-1-ol
;
absolute stereochemistry
;
Pirkle column
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530040405
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