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 Journal Article


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"
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  1. Insik Jeon
    2 Jeon
  2. Isaac Krauss
    6 Krauss
  3. Dongjoo Lee
    6 Lee