CaltechAUTHORS
  A Caltech Library Service

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

[img] PDF - Supplemental Material
See Usage Policy.

1468Kb
[img] PDF - Supplemental Material
See Usage Policy.

833Kb

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20170411-151704722

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:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0022730DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja0022730PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja0022730PublisherSupporting 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 AgencyGrant Number
NIHCA28824
Department of Defense Breast Cancer Research ProgramDAMD 17-97-1-7119
NIHCA-08748
Issue or Number:1
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
Usage Policy: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:03 Oct 2019 17:02

Repository Staff Only: item control page