Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates Journal Article
| Authors: | Keding, S. J.; Endo, A.; Biswas, K.; Zatorski, A.; Coltart, D.; Danishefsky, S. J. |
| Article Title: | Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates |
| Abstract: | A new approach to the synthesis of biologically relevant glycosyl amino acids using a non-natural amino acid as the glycosyl acceptor is described. The procedure involves a glycosylation reaction of a suitable carbohydrate donor with Fmoc-L-hydroxynorleucine benzyl ester. This reaction results in the direct incorporation of the amino acid moiety. The acceptor can be used for the preparation of α- or β-O-linked glycosides depending upon the nature of the glycosyl donor. This method has been applied in the synthesis of six different tumor-associated carbohydrate antigens. © 2003 Elsevier Science Ltd. All rights reserved. |
| Keywords: | unclassified drug; glycosylation; synthesis; carbohydrate; functional group; glycosylamino acid; ester derivative; glycoside; protein glycosylation; carbohydrate-based antitumor vaccines; amino acid derivative; article; hydroxynorleucine |
| Journal Title: | Tetrahedron Letters |
| Volume: | 44 |
| Issue: | 16 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2003-04-14 |
| Start Page: | 3413 |
| End Page: | 3416 |
| Language: | English |
| DOI: | 10.1016/s0040-4039(03)00517-3 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 12 September 2014 -- Source: Scopus |
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