Document Detail


The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars.
MedLine Citation:
PMID:  23348524     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Chia-I Lin; Reid M McCarty; Hung-wen Liu
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Review     Date:  2013-01-25
Journal Detail:
Title:  Chemical Society reviews     Volume:  42     ISSN:  1460-4744     ISO Abbreviation:  Chem Soc Rev     Publication Date:  2013 May 
Date Detail:
Created Date:  2013-04-30     Completed Date:  2013-11-06     Revised Date:  2014-05-23    
Medline Journal Info:
Nlm Unique ID:  0335405     Medline TA:  Chem Soc Rev     Country:  England    
Other Details:
Languages:  eng     Pagination:  4377-407     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amines / chemistry
Anti-Bacterial Agents / biosynthesis,  chemistry
Biological Products / chemistry,  metabolism
Carbohydrates / biosynthesis*,  chemistry
Carbon / chemistry*
Nitrogen / chemistry*
Sulfur / chemistry*
Grant Support
ID/Acronym/Agency:
F32 GM103181/GM/NIGMS NIH HHS; GM035906/GM/NIGMS NIH HHS; GM054346/GM/NIGMS NIH HHS; GM103181/GM/NIGMS NIH HHS; R01 GM035906/GM/NIGMS NIH HHS; R01 GM054346/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amines; 0/Anti-Bacterial Agents; 0/Biological Products; 0/Carbohydrates; 70FD1KFU70/Sulfur; 7440-44-0/Carbon; N762921K75/Nitrogen
Comments/Corrections

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