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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: socky on June 23, 2004, 05:03:26 PM

Title: stereochemistry of C-6 carbon of vancomycin
Post by: socky on June 23, 2004, 05:03:26 PM
Does anyone know why several sources (including the 12th edition of the Merck Index) show that the C-6 carbon atom of vancomycin as an "S" configuration?  Vancomycin is  a glycopeptide antibiotic, a compound based on a defined glycopeptide core.  The structure of the core glycopeptide skeleton was known, and the sterechemistry at the C-6 position of the glycopeptide core was known to be R.

So, which is the correct stereochemistry, S or R?  Can it exist in both configurations, and are both active?