A second generation synthesis of the MBr1 (globo-H) breast tumor antigen

New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages

Jennifer R. Allen, John G. Allen, Xu Feng Zhang, Lawrence Williams, Andrzej Zatorski, Govindaswami Ragupathi, Philip O. Livingston, Samuel J. Danishefsky

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

A new synthesis of the hexasaccharide MBr1 antigen (gloho-H) is reported. A revised construction with improved efficiency was necessary because an anti-cancer vaccine containing this antigen is entering phase II and phase III clinical trials for prostate cancer. The key feature of this second generation synthesis is the preparation of globo-H as its n-pentenyl glycoside. This group serves as an anomeric protecting group and as a linker for bioconjugation to carrier protein. The resultant synthesis allows for the production of suitable quantities of globo-H for clinical trials.

Original languageEnglish (US)
Pages (from-to)1366-1375
Number of pages10
JournalChemistry - A European Journal
Volume6
Issue number8
StatePublished - Apr 14 2000
Externally publishedYes

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Glycosides
Neoplasm Antigens
Antigens
Carbohydrates
Tumors
Proteins
Cancer Vaccines
Vaccines
Carrier Proteins
Globo-H

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Allen, Jennifer R. ; Allen, John G. ; Zhang, Xu Feng ; Williams, Lawrence ; Zatorski, Andrzej ; Ragupathi, Govindaswami ; Livingston, Philip O. ; Danishefsky, Samuel J. / A second generation synthesis of the MBr1 (globo-H) breast tumor antigen : New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages. In: Chemistry - A European Journal. 2000 ; Vol. 6, No. 8. pp. 1366-1375.
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A second generation synthesis of the MBr1 (globo-H) breast tumor antigen : New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages. / Allen, Jennifer R.; Allen, John G.; Zhang, Xu Feng; Williams, Lawrence; Zatorski, Andrzej; Ragupathi, Govindaswami; Livingston, Philip O.; Danishefsky, Samuel J.

In: Chemistry - A European Journal, Vol. 6, No. 8, 14.04.2000, p. 1366-1375.

Research output: Contribution to journalArticle

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