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Issue 42, 2013
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Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins

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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.

Graphical abstract: Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins

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Publication details

The article was received on 01 Aug 2013, accepted on 09 Sep 2013 and first published on 09 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41574K
Citation: Org. Biomol. Chem., 2013,11, 7420-7426
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    Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins

    K. Schiessl, A. Roller and F. Hammerschmidt, Org. Biomol. Chem., 2013, 11, 7420
    DOI: 10.1039/C3OB41574K

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