Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis

The synthesis of biologically relevant glycosyl amino acids from corresponding O-allyl glycosides is described. The procedure involves a cross-metathesis reaction with Fmoc- l-allylglycine benzyl ester, followed by reduction of the resulting olefin via catalytic hydrogenation, with the concomitant r...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 35; pp. 6107 - 6110
Main Authors Biswas, Kaustav, Coltart, Don M., Danishefsky, Samuel J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.08.2002
Elsevier
Subjects
allyl glycosides
carbohydrate-based antitumor vaccines
Chemistry
Chemistry, Organic
cross-metathesis
glycosyl amino acids
Physical Sciences
Science & Technology
carbohydrate-based antitumor vaccines
cross-metathesis
glycosyl amino acids
allyl glycosides
PURSUIT
RING-CLOSING METATHESIS
GLYCOPEPTIDE
ANTICANCER VACCINES
ANTIGENS
TN
CANCER
CATALYSTS
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Summary:The synthesis of biologically relevant glycosyl amino acids from corresponding O-allyl glycosides is described. The procedure involves a cross-metathesis reaction with Fmoc- l-allylglycine benzyl ester, followed by reduction of the resulting olefin via catalytic hydrogenation, with the concomitant release of the free acid. This method has also been applied to the breast and prostate cancer antigen Globo-H, to afford a hexasaccharide glycosyl amino acid that has been previously incorporated in a polyvalent antitumor vaccine. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01336-9