| Exploring and exploiting the reactivity of glucuronic acid donors. | |
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MedLine Citation:
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PMID: 22126096 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic acid esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two protected Streptococcus pneumoniae trisaccharides, in which two similarly protected cellobiouronic acid donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide. |
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Authors:
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Ana Rae de Jong; Bas Hagen; Vincent van der Ark; Herman S Overkleeft; Jeroen Dirk Cornelis Codée; Gijsbert A van der Marel |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-11-29 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Nov |
Date Detail:
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Created Date: 2011-11-30 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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