Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins?
Organic & Biomolecular Chemistry Pub Date: 2013-09-09 DOI: 10.1039/C3OB41574K
Abstract
Fosfazinomycins A and B produced by Streptomyces lavendofoliae share the same phosphonate moiety with one chiral centre of unknown configuration which was determined by synthesising both enantiomers of 2-hydroxy-2-phosphonoacetic acid methyl ester. A chiral cyclic phosphite was reacted with methyl glyoxylate in a Pudovik reaction to give a pair of diastereomeric α-hydroxyphosphonates, which were separated by HPLC. The configurations at C-2 were assigned on the basis of single crystal X-ray structure analysis. Deprotection of these diastereomers furnished the enantiomeric α-hydroxyphosphonic acids, of which the (S)-configured had the same sign of optical rotation as the phosphonic acid moiety of the two fosfazinomycins.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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