Shortcut synthesis of beta-cyclomannin from beta-cyclodextrin

Org Lett. 2006 Dec 7;8(25):5733-6. doi: 10.1021/ol062239b.

Abstract

Beta-cyclomannin, a cyclic oligosaccharide consisting of seven alpha-D-mannosides connected together by the (1-->4) glycoside linkage, has been efficiently synthesized by the OsO4 oxidation of heptakis(2,3-didehydroxy)-beta-cyclodextrin which was prepared from beta-cyclodextrin by a five-step transformation. The novel cyclooligosaccharide not only showed water solubility high enough to meet the requirement for drug formulation but also demonstrated strong binding ability toward guest molecules. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrogen Bonding
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mannosides / chemical synthesis*
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Oxidation-Reduction
  • Spectrophotometry, Ultraviolet
  • beta-Cyclodextrins / chemistry*

Substances

  • Indicators and Reagents
  • Mannosides
  • Oligosaccharides
  • beta-Cyclodextrins
  • beta-cyclomannin