Template effect of vancomycin aglycon in the oxidative oligomerization of 1,6-dithio-d-mannitol: A MALDI-TOF MS and solvent effect study

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Abstract

Oxidative oligomerization of 1,6-dithio-d-mannitol (DTM) using air as oxidant is reported. It was found that both ring and chain oligomers were formed with a degree of polymerization up to 11-12 as determined by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). It was found that the relative amounts of rings to chains were significantly dependent on the solvent employed: in water or in dimethyl formamide (DMF) yielded ring oligomers with a relative amount of higher than 90% (on the average), and almost exclusive formation of chain oligomers was observed in methanol or in dioxane. The oxidative oligomerization of DTM was also carried out in the presence of vancomycin aglycon as a template. It was observed that in water the vancomycin aglycon induced the exclusive formation of chain oligomers from DTM. The non-covalent, strong interaction existing between the vancomycin aglycon and the chain dimer of DTM was further supported by electrospray ionization mass spectrometry (ESI-MS).

Original languageEnglish
Pages (from-to)1-7
Number of pages7
JournalCarbohydrate Polymers
Volume73
Issue number1
DOIs
Publication statusPublished - Jul 4 2008

Keywords

  • 1,6-Dithio-d-mannitol
  • ESI-MS
  • MALDI-TOF MS
  • Oxidative polycondensation
  • Ring-chain equilibrium

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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