New applications of the n-pentenyl glycoside method in the synthesis and immunoconjugation of fucosyl GM1: A highly tumor-specific antigen associated with small cell lung carcinoma Journal Article
| Authors: | Allen, J. R.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. |
| Article Title: | New applications of the n-pentenyl glycoside method in the synthesis and immunoconjugation of fucosyl GM1: A highly tumor-specific antigen associated with small cell lung carcinoma |
| Abstract: | The synthesis of fucosyl GM1 pentenyl glycoside 1b, and its conjugation to carrier protein KLH to give lc is related. Bioconjugation of 1b was realized using the pendant olefin contained in the reducing end n-pentenyl glycoside (NPG). The key step of the endeavor is a stereospecific [3 + 3] coupling reaction using our sulfonamido glycosidation protocol (see 23 + 12 → 15). Pre-installation of the NPG was required for an optimal [3 + 3] coupling yield and to allow for smooth global deprotection. The synthesis and subsequent immunocharacterization served to confirm the assigned structure of the natural tumor antigen. Fully synthetic conjugate lc advances our program toward the goal of using a synthetic vaccine containing fucosyl GM1 as a potential target for immune attack against small cell lung carcinoma. |
| Keywords: | lung small cell cancer; vaccination; chemical structure; stereospecificity; chemical reaction; conjugation; glycoside; glycoprotein synthesis; alkene; article |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 121 |
| Issue: | 47 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 1999-12-01 |
| Start Page: | 10875 |
| End Page: | 10882 |
| Language: | English |
| DOI: | 10.1021/ja992594f |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 16 August 2016 -- Source: Scopus |
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539Danishefsky -
228Livingston
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