Authors: | Jeon, I.; Lee, D.; Krauss, I. J.; Danishefsky, S. J. |
Article Title: | A new model for the presentation of tumor-associated antigens and the quest for an anticancer vaccine: A solution to the synthesis challenge via ring-closing metathesis |
Abstract: | Fully synthetic, carbohydrate-based antitumor vaccine candidates have been synthesized in highly clustered modes. Multiple copies of tumor-associated carbohydrate antigens, Tn and STn, were assembled on a single cyclic peptide scaffold in a highly convergent manner. Ring-closing metathesis-mediated incorporation of an internal cross-linker was also demonstrated. In particular, this rigidified cross-linked construct would enhance a cluster-recognizing antibody response by retaining an appropriate distance between glycans attached to the peptide platform. Details of the design and synthesis of highly clustered antigens are described herein. © 2009 American Chemical Society. |
Keywords: | unclassified drug; tumor antigen; antigen presentation; amines; drug research; immune response; antigens; cancer vaccine; cancer vaccines; tumors; antibody response; peptides; synthesis (chemical); antigens, tumor-associated, carbohydrate; anti-tumors; appropriate distances; crosslinker; cyclic peptides; glycans; new model; ring closing metathesis; carbohydrates; carbohydrate antigen; glycan derivative; glycopeptide; stn antigen; tn antigen; antibody formation; glycopeptides; peptides, cyclic |
Journal Title: | Journal of the American Chemical Society |
Volume: | 131 |
Issue: | 40 |
ISSN: | 0002-7863 |
Publisher: | American Chemical Society |
Date Published: | 2009-10-14 |
Start Page: | 14337 |
End Page: | 14344 |
Language: | English |
DOI: | 10.1021/ja9052625 |
PUBMED: | 19746915 |
PROVIDER: | scopus |
PMCID: | PMC2758925 |
DOI/URL: | |
Notes: | --- - "Cited By (since 1996): 1" - "Export Date: 30 November 2010" - "CODEN: JACSA" - "Source: Scopus" |