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

49 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

Fingerprint

Galactose
Nuclear magnetic resonance spectroscopy
Esters
Magnetic Resonance Spectroscopy
Kinetics
Planning
Acids

Keywords

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

Cite this

Roslund, Mattias U. ; Aitio, Olli ; Wärnå, Johan ; Maaheimo, Hannu ; Murzin, Dmitry Yu. ; Leino, Reko. / Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 27. pp. 8769-8772.
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Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations. / Roslund, Mattias U.; Aitio, Olli; Wärnå, Johan; Maaheimo, Hannu; Murzin, Dmitry Yu.; Leino, Reko.

In: Journal of the American Chemical Society, Vol. 130, No. 27, 2008, p. 8769-8772.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Acyl group migration and cleavage in selectively protected β-d-galactopyranosides as studied by NMR spectroscopy and kinetic calculations

AU - Roslund, Mattias U.

AU - Aitio, Olli

AU - Wärnå, Johan

AU - Maaheimo, Hannu

AU - Murzin, Dmitry Yu.

AU - Leino, Reko

PY - 2008

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AB - 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.

KW - acyltransferases

KW - acyl group

KW - acyl group migration

KW - esters

KW - carbohydrate syntheses

U2 - 10.1021/ja801177s

DO - 10.1021/ja801177s

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