Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations

Mattias U. Roslund, Olli Aitio, Johan Wärnå, Hannu Maaheimo, Dmitry Yu. Murzin, Reko Leino

Research output: Contribution to journalArticleScientificpeer-review

60 Citations (Scopus)

Abstract

The migration of acetyl, pivaloyl, and benzoyl protective groups and their relative stabilities at variable pH for a series of β-d-galactopyranoses were studied by NMR spectroscopy. The clockwise and counterclockwise migration rates for the different ester groups were accurately determined by use of a kinetic model. The results presented provide new insights into the acid and base stabilities of commonly used ester protecting groups and the phenomenon of acyl group migration and may prove useful in the planning of synthesis strategies.
Original languageEnglish
Pages (from-to)8769-8772
Number of pages4
JournalJournal of the American Chemical Society
Volume130
Issue number27
DOIs
Publication statusPublished - 2008
MoE publication typeA1 Journal article-refereed

Keywords

  • acyltransferases
  • acyl group
  • acyl group migration
  • esters
  • carbohydrate syntheses

Fingerprint Dive into the research topics of 'Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations'. Together they form a unique fingerprint.

  • Cite this