Document Detail

Chemoenzymatic synthesis of differentially protected 3-deoxysugars.
MedLine Citation:
PMID:  21124399     Owner:  NLM     Status:  MEDLINE    
3-Deoxysugars are important constituents of complex carbohydrates. For example, 2-keto-3-deoxy-D-manno-octulosonic acid (KDO) is an essential component of lipopolysaccharides in Gram-negative bacteria, 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN) is widely found in carbohydrates of the bacterial cell wall and in lower vertebrates, and sialic acid is a common cap of mammalian glycoproteins. Although ready access to such sugars would benefit the creation of vaccine candidates, antibiotics and small-molecule drugs, their chemical synthesis is difficult. Here we present a simple chemoenzymatic method for preparing differentially protected 3-deoxysugar derivatives from readily available starting materials. It exploits the promiscuous aldolase activity of the enzyme macrophomate synthase (MPS) to add pyruvate enolate diastereoselectively to a wide range of structurally complex aldehydes. A short synthesis of KDN illustrates the utility of this approach. Enzyme promiscuity, which putatively fosters large functional leaps in natural evolution, has great promise as a source of synthetically useful catalytic transformations.
Dennis G Gillingham; Pierre Stallforth; Alexander Adibekian; Peter H Seeberger; Donald Hilvert
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-01-17
Journal Detail:
Title:  Nature chemistry     Volume:  2     ISSN:  1755-4349     ISO Abbreviation:  Nat Chem     Publication Date:  2010 Feb 
Date Detail:
Created Date:  2010-12-02     Completed Date:  2011-01-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101499734     Medline TA:  Nat Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  102-5     Citation Subset:  IM    
Laboratory of Organic Chemistry, ETH Zurich, 8093 Zurich, Switzerland.
Data Bank Information
Bank Name/Acc. No.:
PubChem-Substance/85845735;  85845736;  85845737;  85845738;  85845739;  85845740;  85845741;  85845742;  85845743;  85845744;  85845745;  85845746;  85845747;  85845748;  85845749;  85845750;  85845751;  85845752;  85845753;  85845754;  85845755;  85845756;  85845757;  85845758;  85845759;  85845760;  85845761;  85845762;  85845763;  85845764;  85845765;  85845766;  85845767;  85845768
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MeSH Terms
Carbohydrates / biosynthesis*,  chemistry*
Catalytic Domain
Models, Molecular
Multienzyme Complexes / chemistry,  metabolism*
Pyruvates / metabolism
Substrate Specificity
Reg. No./Substance:
0/Carbohydrates; 0/Multienzyme Complexes; 0/Pyruvates; 0/macrophomate synthase
Comment In:
Nat Chem. 2010 Feb;2(2):85-6   [PMID:  21124396 ]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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