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Issue 10, 2013
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The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

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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

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Publication details

The article was received on 24 Oct 2012 and first published on 25 Jan 2013


Article type: Review Article
DOI: 10.1039/C2CS35438A
Chem. Soc. Rev., 2013,42, 4377-4407

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    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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