Construction of carbohydrate-based antitumor vaccines: Synthesis of glycosyl amino acids by olefin cross-metathesis Journal Article
| Authors: | Biswas, K.; Coltart, D.; Danishefsky, S. J. |
| Article Title: | Construction of carbohydrate-based antitumor vaccines: Synthesis of glycosyl amino acids by olefin cross-metathesis |
| Abstract: | 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. © 2002 Published by Elsevier Science Ltd. |
| Keywords: | unclassified drug; drug synthesis; tumor antigen; cancer vaccine; glycosylation; catalysis; vaccine production; catalyst; chemical reaction; carbohydrate; ester derivative; hydrogenation; glycoside; alkene; carbohydrate-based antitumor vaccines; aminoglycoside derivative; cross-metathesis; article; allyl glycosides; glycosyl amino acids; 9 fluorenylmethoxycarbonylallylglycine benzyl ester; cross metathesis |
| Journal Title: | Tetrahedron Letters |
| Volume: | 43 |
| Issue: | 35 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2002-08-26 |
| Start Page: | 6107 |
| End Page: | 6110 |
| Language: | English |
| DOI: | 10.1016/s0040-4039(02)01336-9 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 14 November 2014 -- Source: Scopus |
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