Issue 10, 2013

The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

Abstract

Carbohydrates serve many structural and functional roles in biology. While the majority of monosaccharides are characterized by the chemical composition (CH2O)n, modifications including deoxygenation, C-alkylation, amination, O- and N-methylation, which are characteristic of many sugar appendages of secondary metabolites, are not uncommon. Interestingly, some sugar molecules are formed via modifications including amine oxidation, sulfur incorporation, and “high-carbon” chain attachment. Most of these unusual sugars have been identified over the past several decades as components of microbially produced natural products, although a few high-carbon sugars are also found in the lipooligosaccharides of the outer cell walls of Gram-negative bacteria. Despite their broad distribution in nature, these sugars are considered “rare” due to their relative scarcity. The biosynthetic steps that underlie their formation continue to perplex researchers to this day and many questions regarding key transformations remain unanswered. This review will focus on our current understanding of the biosynthesis of unusual sugars bearing oxidized amine substituents, thio-functional groups, and high-carbon chains.

Graphical abstract: The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

Article information

Article type
Review Article
Submitted
24 Oct 2012
First published
25 Jan 2013

Chem. Soc. Rev., 2013,42, 4377-4407

The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

Chia-I. Lin, R. M. McCarty and H. Liu, Chem. Soc. Rev., 2013, 42, 4377 DOI: 10.1039/C2CS35438A

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