The Synthesis and Biological Characterization of Acetal-Free Mimics of the Tumor-Associated Carbohydrate Antigens

Document Type

Article

Publication Date

1-1-2017

Publication Title

Advances in Carbohydrate Chemistry and Biochemistry

Volume

74

First Page

137

Keywords

Acetal-free carbohydrate, C-glycoside, Cancer immunotherapy, Cancer vaccine, Carbasugar, sTn, TF, Tn, Tumor-associated carbohydrate antigens

Last Page

237

Abstract

Carcinomas express unique carbohydrates, known as tumor-associated carbohydrate antigens (TACAs), on their surface. These are potential targets for anticancer vaccines; however, to date, no such vaccine has reached the clinic. One factor that may complicate the success of this effort is the lability of the glycosidic bond. Acetal-free carbohydrates are analogues that lack the glycosidic linkage by replacing either the endo or exo oxygen with a methylene. This chapter summarizes the seminal syntheses of the mucin TACAs, provides an overview of common techniques for the synthesis of carbasugars and C-glycosides, reviews the syntheses published to date of acetal-free TACA analogues, and provides an overview of their observed biological activity. We conclude by offering a summation of the challenges remaining to the field biologically and the potential that acetal-free TACAs have of answering several basic questions in carbohydrate immunology.

DOI

10.1016/bs.accb.2017.10.003

ISSN

00652318

PubMed ID

29173726

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