Document Detail


Chemoselective synthesis of sialic acid 1,7-lactones.
MedLine Citation:
PMID:  20704429     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The chemoselective synthesis of the 1,7-lactones of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-d-glycero-d-galacto-nononic acid is accomplished in two steps: a simple treatment of the corresponding free sialic acid with benzyloxycarbonyl chloride and a successive hydrogenolysis of the formed 2-benzyloxycarbonyl 1,7-lactone. The instability of the 1,7-lactones to protic solvents has been also evidenced together with the rationalization of the mechanism of their formation under acylation conditions. The results permit to dispose of authentic 1,7-sialolactones to be used as reference standards and of a procedure useful for the preparation of their isotopologues to be used as inner standards in improved analytical procedures for the gas liquid chromatography-mass spectrometry (GLC-MS) analysis of 1,7-sialolactones in biological media.
Authors:
Pietro Allevi; Paola Rota; Raffaella Scaringi; Raffaele Colombo; Mario Anastasia
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Aug 
Date Detail:
Created Date:  2010-08-13     Completed Date:  2010-11-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  5542-8     Citation Subset:  IM    
Affiliation:
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università degli Studi di Milano, Via Saldini 50, I-20133 Milano, Italy.
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MeSH Terms
Descriptor/Qualifier:
Carbohydrate Conformation
Lactones / chemical synthesis*,  chemistry
Sialic Acids / chemical synthesis*,  chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Lactones; 0/Sialic Acids

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