The antituberculosis, antitumor, multibranched dodecafuranoarabinan of Mycobacterium species has been assembled from a single n-pentenylfuranoside source

Chem Commun (Camb). 2005 Feb 21:(7):862-4. doi: 10.1039/b413694b. Epub 2005 Jan 5.

Abstract

An n-pentenyl furanosyl-1,2-orthoester can function as a donor or be rearranged leading to an n-pentenyl furanoside acceptor which is glycosylated by its progenitor, regioselectively or doubly, thereby enabling rapid fabrication of a multibranched dodecasaccharide, known to possess a wide variety of biological interactions.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Carbohydrate Conformation
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Sequence Data
  • Mycobacterium / chemistry*
  • Mycobacterium / classification
  • Pentoses / chemistry
  • Polysaccharides / chemical synthesis*
  • Polysaccharides / chemistry
  • Species Specificity
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Antitubercular Agents
  • Bridged Bicyclo Compounds, Heterocyclic
  • Furans
  • Pentoses
  • Polysaccharides