Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method

Kim, Hyunjin M. and Kim, In Jong and Danishefsky, Samuel J. (2001) Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method. Journal of the American Chemical Society, 123 (1). pp. 35-48. ISSN 0002-7863. doi:10.1021/ja0022730. https://resolver.caltech.edu/CaltechAUTHORS:20170411-151704722

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Abstract

The total syntheses of two octasaccharide antigens isolated from human milk, 1 and 2, and their corresponding allyl glycosides, 3 and 4, have been achieved by utilizing the glycal method. Convergent assembly of the core hexasaccharides and concurrent introduction of two α-l-fucosyl moieties at the late stage of the syntheses provided these complex carbohydrates in a concise manner. With synthetic material obtained, biological evaluations of these antigens as potential gastrointestinal cancer immunotherapeutic agents have been initiated.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja0022730	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja0022730	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja0022730	Publisher	Supporting Information

Additional Information:

© 2001 American Chemical Society. Received 23 June 2000. Published online 14 December 2000. Published in print 1 January 2001. This work was supported by the National Institutes of Health (Grant No. CA28824). H.M.K. gratefully acknowledges the U.S. Army for a Department of Defense Breast Cancer Predoctoral/Graduate Fellowship (No. DAMD 17-97-1-7119). We thank Dr. George Sukenick for providing mass spectral and NMR analyses (SKI Core Grant No. CA-08748).

Funders:

Funding Agency	Grant Number
NIH	CA28824
Department of Defense Breast Cancer Research Program	DAMD 17-97-1-7119
NIH	CA-08748

Issue or Number:

DOI:

10.1021/ja0022730

Record Number:

CaltechAUTHORS:20170411-151704722

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170411-151704722

Official Citation:

Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method Hyunjin M. Kim, In Jong Kim, and Samuel J. Danishefsky Journal of the American Chemical Society 2001 123 (1), 35-48 DOI: 10.1021/ja0022730

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No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

76521

Collection:

CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

12 Apr 2017 16:05

Last Modified:

15 Nov 2021 17:00

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