Synthesis of non-natural o-glycosylamino acids derived from n-pentenyl glycosides; Model studies and proof of principle for glycopeptide synthesis Journal Article
| Authors: | Allen, J. R.; Danishefsky, S. J. |
| Article Title: | Synthesis of non-natural o-glycosylamino acids derived from n-pentenyl glycosides; Model studies and proof of principle for glycopeptide synthesis |
| Abstract: | Model studies on the transformation of the olefinic unit contained in n-pentenyl glycosides (NPGs) to glycoamino acids is described. The methodology involves a Horner-Emmons olefination with a protected glycine derived phosphonate, followed by asymmetric hydrogenation using Du-PHOS catalyst system. A variety of protecting group schemes have been investigated and their stereoselectivity in the hydrogenation reaction determined. With N-Boc and C-TSE ester protection, the diastereoselectivity in the reaction was measured by 1H NMR analysis with "racemic" product as a comparison. These modified glycoamino acids are also useful for peptide synthesis. The methodology appears to be general and was extended to include the synthesis a glycoamino acid containing the complex hexasaccharide Globo-H. |
| Keywords: | carbohydrates; glycopeptides; glycoconjugates; asymmetric catalysis; hydrogenations |
| Journal Title: | Advanced Synthesis and Catalysis |
| Volume: | 342 |
| Issue: | 8 |
| ISSN: | 1615-4150 |
| Publisher: | Wiley V C H Verlag Gmbh |
| Date Published: | 2000-10-01 |
| Start Page: | 736 |
| End Page: | 744 |
| Language: | English |
| PROVIDER: | scopus |
| DOI: | 10.1002/1521-3897(200010)342:8<736::AID-PRAC736>3.0.CO;2-%23 |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
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