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

doi:10.1021/ja801177s

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 journal › Article › Scientific › peer-review

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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 language	English
Pages (from-to)	8769-8772
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	130
Issue number	27
DOIs	https://doi.org/10.1021/ja801177s
Publication status	Published - 2008
MoE publication type	A1 Journal article-refereed

Keywords

acyltransferases
acyl group
acyl group migration
esters
carbohydrate syntheses

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10.1021/ja801177s

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

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.",

keywords = "acyltransferases, acyl group, acyl group migration, esters, carbohydrate syntheses",

author = "Roslund, {Mattias U.} and Olli Aitio and Johan W{\"a}rn{\aa} and Hannu Maaheimo and Murzin, {Dmitry Yu.} and Reko Leino",

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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

Y1 - 2008

N2 - 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.

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

M3 - Article

SN - 0002-7863

VL - 130

SP - 8769

EP - 8772

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27

ER -

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

Abstract

Keywords

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