Synthesis of selected LeY and KH-1 analogues: A medicinal chemistry approach to vaccine optimization Journal Article
| Authors: | Spassova, M. K.; Bornmann, W. G.; Ragupathi, G.; Sukenick, G.; Livingston, P. O.; Danishefsky, S. J. |
| Article Title: | Synthesis of selected LeY and KH-1 analogues: A medicinal chemistry approach to vaccine optimization |
| Abstract: | (Chemical Equation Presented) As part of our ongoing anticancer vaccine program, we recently found that antibodies generated in response to the KH-1-KLH construct recognized not only KH-1 antigen but also the Lewis Y (Le y) antigen as well, with antibody titer levels much higher than those observed after immunization with individual Ley-KLH vaccine constructs. In an attempt to explore the structure-antigenic relationship of these carbohydrate epitopes, several analogues of both KH-1 and Ley were synthesized. A convergent synthetic approach to the analogues was designed on the basis of well-established glycal methodology, employing a minimum number of building blocks to generate competent antigens with high stereoselectivity and reasonable yield. © 2005 American Chemical Society. |
| Keywords: | unclassified drug; methodology; chemistry, pharmaceutical; antineoplastic activity; drug structure; drug design; drug synthesis; structure activity relation; structure-activity relationship; tumor antigen; immunology; chemistry; antigens; cancer vaccine; cancer vaccines; tumors; epitope; vaccines, synthetic; immunological adjuvant; chemical structure; molecular structure; antibodies; vaccine production; adjuvants, immunologic; biochemistry; synthesis; carbohydrate analysis; synthesis (chemical); antigens, tumor-associated, carbohydrate; carbohydrate sequence; carbohydrates; recombinant vaccine; vaccines; stereochemistry; gene construct; lewis blood-group system; immunization; oligosaccharide; oligosaccharides; glycals; blood group lewis system; lewis y antigen; antibody titer levels; carbohydrate epitopes; medicinal chemistry; drug analog; kh 1 analog; lewis y analog; antigen kh 1; antigen kh-1 |
| Journal Title: | Journal of Organic Chemistry |
| Volume: | 70 |
| Issue: | 9 |
| ISSN: | 0022-3263 |
| Publisher: | American Chemical Society |
| Date Published: | 2005-04-29 |
| Start Page: | 3383 |
| End Page: | 3395 |
| Language: | English |
| DOI: | 10.1021/jo048016l |
| PUBMED: | 15844973 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 17" - "Export Date: 24 October 2012" - "CODEN: JOCEA" - "Source: Scopus" |
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144Ragupathi -
539Danishefsky -
23Sukenick -
25
Spassova -
228Livingston
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