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 J. Williams; Andrzej Zatorski; Govindaswami Ragupathi; Philip O. Livingston; Samuel J. Danishefsky

doi:10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b

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 J. Williams, Andrzej Zatorski, Govindaswami Ragupathi, Philip O. Livingston, Samuel J. Danishefsky

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

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 language	English (US)
Pages (from-to)	1366-1375
Number of pages	10
Journal	Chemistry - A European Journal
Volume	6
Issue number	8
DOIs	https://doi.org/10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b
State	Published - Apr 14 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Keywords

Antigens
Carbohydrates
Glycoconjugates
Glycosides
Immunology

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10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b

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Allen, J. R., Allen, J. G., Zhang, X. F., Williams, L. J., Zatorski, A., Ragupathi, G., Livingston, P. O., & Danishefsky, S. J. (2000). 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. Chemistry - A European Journal, 6(8), 1366-1375. https://doi.org/10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b

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title = "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",

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.",

keywords = "Antigens, Carbohydrates, Glycoconjugates, Glycosides, Immunology",

author = "Allen, {Jennifer R.} and Allen, {John G.} and Zhang, {Xu Feng} and Williams, {Lawrence J.} and Andrzej Zatorski and Govindaswami Ragupathi and Livingston, {Philip O.} and Danishefsky, {Samuel J.}",

year = "2000",

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doi = "10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b",

language = "English (US)",

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}

Allen, JR, Allen, JG, Zhang, XF, Williams, LJ, Zatorski, A, Ragupathi, G, Livingston, PO & Danishefsky, SJ 2000, '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', Chemistry - A European Journal, vol. 6, no. 8, pp. 1366-1375. https://doi.org/10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b

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

Research output: Contribution to journal › Article › peer-review

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T2 - New application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages

AU - Allen, Jennifer R.

AU - Allen, John G.

AU - Zhang, Xu Feng

AU - Williams, Lawrence J.

AU - Zatorski, Andrzej

AU - Ragupathi, Govindaswami

AU - Livingston, Philip O.

AU - Danishefsky, Samuel J.

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AB - 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.

KW - Antigens

KW - Carbohydrates

KW - Glycoconjugates

KW - Glycosides

KW - Immunology

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Allen JR, Allen JG, Zhang XF, Williams LJ, Zatorski A, Ragupathi G et al. 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. Chemistry - A European Journal. 2000 Apr 14;6(8):1366-1375. doi: 10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.3.co;2-b

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

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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