Document Detail


One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities.
MedLine Citation:
PMID:  17406495     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Chemoenzymatic synthesis, which combines the flexibility of chemical synthesis and the high selectivity of enzymatic synthesis, is a powerful approach to obtain complex carbohydrates. It is a preferred method for synthesizing sialic acid-containing structures, including those with diverse naturally occurring and non-natural sialic acid forms, different sialyl linkages and different glycans that link to the sialic acid. Starting from N-acetylmannosamine, mannose or their chemically or enzymatically modified derivatives, sialic acid aldolase-catalyzed condensation reaction leads to the formation of sialic acids and their derivatives. These compounds are subsequently activated by a CMP-sialic acid synthetase and transferred to a wide range of suitable acceptors by a suitable sialyltransferase for the formation of sialosides containing natural and non-natural functionalities. The three-enzyme coupled synthesis of sialosides can be carried out in one pot without the isolation of intermediates. The time for synthesis is 4-18 h. Purification and characterization of the product can be completed within 2-3 d.
Authors:
Hai Yu; Harshal A Chokhawala; Shengshu Huang; Xi Chen
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Nature protocols     Volume:  1     ISSN:  1750-2799     ISO Abbreviation:  Nat Protoc     Publication Date:  2006  
Date Detail:
Created Date:  2007-04-04     Completed Date:  2007-10-23     Revised Date:  2014-09-17    
Medline Journal Info:
Nlm Unique ID:  101284307     Medline TA:  Nat Protoc     Country:  England    
Other Details:
Languages:  eng     Pagination:  2485-92     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Escherichia coli K12 / enzymology
Oxo-Acid-Lyases / metabolism
Pasteurella multocida / enzymology
Photobacterium / enzymology
Sialic Acids / chemical synthesis*,  chemistry*,  isolation & purification
Sialyltransferases / metabolism
Trisaccharides / chemical synthesis*,  chemistry,  isolation & purification
Grant Support
ID/Acronym/Agency:
R01 GM076360/GM/NIGMS NIH HHS; R01 GM076360-01/GM/NIGMS NIH HHS; R01GM076360/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Sialic Acids; 0/Trisaccharides; EC 2.4.99.-/Sialyltransferases; EC 4.1.3.-/Oxo-Acid-Lyases; EC 4.1.3.3/N-acetylneuraminate lyase
Comments/Corrections

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