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Article
Syntheses of small cluster oligosaccharide mimetics
ARKIVOC
  • Andreas H. Franz, University of the Pacific
  • Paul H. Gross, University of the Pacific
  • Vyacheslav V. Samoshin, University of the Pacific
Document Type
Article
Department
Chemistry
DOI
10.3998/ark.5550190.0009.110
Publication Date
1-1-2008
Disciplines
Abstract
We designed multiple Small Cluster Oligosaccharide Mimetics (SCOMs) - potential glycosidase inhibitors - to be metabolically stable and small enough to enter cells or bacteria. Therefore, minimal scaffolds (urea, amide, ammonia) or simply non-glycosidic linkages of carbohydrate structures were central to our synthetic strategy, including: (a) coupling of several natural carbohydrate precursors; (b) total syntheses of aminomethyl tetrahydropyrans and their chiral amides with quinic acid; (c) glycopyranosyl cyanide reduction to prepare crowded clusters on a urea scaffold; (d) total syntheses via cycloadditions leading to amide-linked C-glycosides; (e) reduction of nitromethyl C-glycosides; and (f) a synthesis of hydroxylated 1,2- cyclohexanedicarboxylic acids.
Creative Commons License
Creative Commons Attribution 4.0
Citation Information
Andreas H. Franz, Paul H. Gross and Vyacheslav V. Samoshin. "Syntheses of small cluster oligosaccharide mimetics" ARKIVOC Vol. 2008 Iss. 1 (2008) p. 231 - 308 ISSN: 1551-7012
Available at: http://works.bepress.com/andreas-franz/60/