Journal
CARBOHYDRATE RESEARCH
Volume 343, Issue 1, Pages 18-30Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2007.10.006
Keywords
aldonolactone; mannonolactone; gluconolactone; C-2 epimerization; magnesium iodide
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The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.
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