ChemInform Abstract: A Mechanistic Analysis of C—O Bond Cleavage Events with a Comparison to 3,6‐Dideoxysugar Formation

Abstract

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Mechanisms and structures of vitamin B6-dependent enzymes involved in deoxy sugar biosynthesis

“…Most naturally occurring deoxyhexoses are deoxygenated at the C6 position; however, further deoxygention at C2, C3 and C4 is also observed [3,6,59]. Although the 2,6-dideoxyhexoses are by far the most abundant deoxy sugars found in natural products, deoxy sugars featuring different patterns of deoxygenation, e.g., 3,6-dideoxy hexoses, are commonly found as components of Gram negative lipopolysaccharide (LPS) O -antigens, where their structural variety contributes to their complex roles in cellular recognition and virulence [60,61]. Other alternatively deoxygenated sugars such as 4,6-dideoxy, 2,3,6-trideoxy, 2,4,6-trideoxy, 3,4,6-trideoxy, and 2,3,4,6-tetradeoxy hexoses are much less abundant and are found mainly as components of bioactive natural products, where they are often found to be essential to the biological efficacy or target specificity of the natural products they decorate [1–5,10,11].…”