Document Detail

Pursuit of optimal carbohydrate-based anticancer vaccines: preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewis(y) antigens.
MedLine Citation:
PMID:  11456809     Owner:  NLM     Status:  MEDLINE    
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 Le(y) 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.
J R Allen; C R Harris; S J Danishefsky
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  123     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2001 Mar 
Date Detail:
Created Date:  2001-07-17     Completed Date:  2001-10-11     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1890-7     Citation Subset:  IM    
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10021, USA.
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MeSH Terms
Amino Sugars / chemical synthesis*
Antigens, Tumor-Associated, Carbohydrate / chemistry*
Cancer Vaccines / chemical synthesis*,  chemistry*
Carbohydrate Conformation
Carbohydrate Sequence
Glycoconjugates / chemical synthesis*
Glycopeptides / chemical synthesis*
Immunotherapy / methods
Lewis Blood-Group System / chemistry*
Polysaccharides / chemical synthesis*
Vaccines, Conjugate / chemistry*
Grant Support
Reg. No./Substance:
0/Amino Sugars; 0/Antigens, Tumor-Associated, Carbohydrate; 0/Cancer Vaccines; 0/Glycoconjugates; 0/Glycopeptides; 0/Lewis Blood-Group System; 0/Lewis Y antigen; 0/Polysaccharides; 0/Tn antigen; 0/Vaccines, Conjugate; 0/globo H-keyhole limpet hemocyanin QS-21 vaccine

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