Pursuit of optimal carbohydrate-based anticancer vaccines: Preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewisy antigens Journal Article

  


Authors: Allen, J. R.; Harris, C. R.; Danishefsky, S. J.
Article Title: Pursuit of optimal carbohydrate-based anticancer vaccines: Preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewisy antigens
Abstract: A novel preparation of nonnatural glycoamino acids starting from n-pentenyl glycosides is described. The approach involves a Horner - Emmons olefination with a suitably protected glycine-derived phosphonate, followed by catalytic asymmetric hydrogenation, which proceeds with excellent diastereomeric selectivity. The synthetic methodology was useful for the preparation of glycoamino acids containing the Tn antigen, the MBr1 antigen (Globo-H); the Ley antigen, and lactose. These glycoamino acids can also serve as units for peptide synthesis. The synthesis of polyvalent glycopeptides containing three different antitumor antigens is described (28 and 29), and these have been prepared for conjugation to carrier protein in order to access the immunogenicity for tumor immunotherapy applications.
Keywords: carrier protein; unclassified drug; cancer immunotherapy; tumor antigen; antigen; immunotherapy; cancer vaccine; cancer vaccines; immunogenicity; cancer immunization; catalysis; polysaccharides; antigens, tumor-associated, carbohydrate; carbohydrate sequence; carbohydrate antigen; glycopeptide; tn antigen; glycopeptides; peptide synthesis; lewis blood-group system; vaccines, conjugate; phosphonic acid derivative; carbohydrate conformation; hydrogenation; blood group lewis system; glycoconjugates; lactose; article; amino sugars; antigen mbr1
Journal Title: Journal of the American Chemical Society
Volume: 123
Issue: 9
ISSN: 0002-7863
Publisher: American Chemical Society  
Date Published: 2001-03-07
Start Page: 1890
End Page: 1897
Language: English
DOI: 10.1021/ja002779i
PUBMED: 11456809
PROVIDER: scopus
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-0035820048&partnerID=40&md5=864ff58c2b2950986db1bd75ee84d155
Notes: Export Date: 21 May 2015 -- Source: Scopus
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MSK Authors
  1. Jennifer R Allen
    11 Allen
  2. Christina R Harris
    13 Harris
  3. Samuel J Danishefsky
    539 Danishefsky
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