Document Detail


Accessibility of N-acyl-D-mannosamines to N-acetyl-D-neuraminic acid aldolase.
MedLine Citation:
PMID:  15280054     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives of D-mannosamine were prepared, and their accessibility to NeuNAc aldolase was quantitatively investigated. The N-propionyl-, N-butanoyl-, N-iso-butanoyl-, N-pivaloyl-, and N-phenylacetyl-D-mannosamines proved to be as good substrates as, or even better than, the natural N-acetyl-D-mannosamine, while the N-trifluoropropionyl and benzoyl derivatives were poor. It was proposed that the electronic effects might have a significant influence on the enzymatic aldol condensation reaction of D-mannosamine derivatives, with electron-deficient acyl groups having a negative impact. The results suggest that N-propionyl-, N-butanoyl-, N-iso-butanoyl-, and N-phenylacetyl-D-mannosamines may be employed to bioengineer NeuNAc on cells.
Authors:
Yanbin Pan; Tiffany Ayani; Janos Nadas; Shouming Wen; Zhongwu Guo
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Carbohydrate research     Volume:  339     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  2004 Aug 
Date Detail:
Created Date:  2004-07-28     Completed Date:  2005-08-11     Revised Date:  2013-06-09    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  2091-100     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, OH 44106, USA.
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MeSH Terms
Descriptor/Qualifier:
Carbohydrate Conformation
Fructose-Bisphosphate Aldolase / chemistry*
Hexosamines / chemical synthesis*,  chemistry
Neuraminic Acids / chemical synthesis*,  chemistry
Time Factors
Grant Support
ID/Acronym/Agency:
1R01 CA95142/CA/NCI NIH HHS; R01 CA095142-01/CA/NCI NIH HHS; R01 CA095142-02/CA/NCI NIH HHS; R01 CA095142-03/CA/NCI NIH HHS; R01 CA095142-04/CA/NCI NIH HHS
Chemical
Reg. No./Substance:
0/Hexosamines; 0/Neuraminic Acids; 2636-92-2/mannosamine; EC 4.1.2.13/Fructose-Bisphosphate Aldolase
Comments/Corrections

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