| Chemoselective synthesis of sialic acid 1,7-lactones. | |
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MedLine Citation:
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PMID: 20704429 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Pietro Allevi; Paola Rota; Raffaella Scaringi; Raffaele Colombo; Mario Anastasia |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-08-13 Completed Date: 2010-11-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 5542-8 Citation Subset: IM |
Affiliation:
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Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università degli Studi di Milano, Via Saldini 50, I-20133 Milano, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Carbohydrate Conformation Lactones / chemical synthesis*, chemistry Sialic Acids / chemical synthesis*, chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Lactones; 0/Sialic Acids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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