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Synthesis of an Aminooxy Derivative of the Trisaccharide Globotriose Gb3

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JOURNAL OF CARBOHYDRATE CHEMISTRY
卷 33, 期 7-8, 页码 381-394

出版社

TAYLOR & FRANCIS INC
DOI: 10.1080/07328303.2014.925913

关键词

Aminooxy sugar; Gb3 trisaccharide; Shiga toxin; Glycosylation

资金

  1. National Institute of Health [NCI-R01 CA156661-01]

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The synthesis of -aminooxy trisaccharide moiety [-d-Gal-(1,4)--d-Gal-(1,4)--d-Glc--aminooxy], related to the cell surface globotriaosylceramide (Gb3) receptor of the B subunit of the AB(5) Shiga toxin of Shigella dysenteriae, has been carried out for the first time in 11 steps with a 15% overall isolated yield. A highlight of this work entails utilizing chemically compatible synthetic transformations, including those related to glycosylation, incorporative of the succinimidyl moiety as a precursor to the aminooxy Gb3 derivative. The fully deprotected trisaccharide aminooxy compound was reacted with a carbonyl compound, leading to oxime formation in quantitative yield, which underscores the importance for future glyco-conjugations.

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