Regio- and Stereoselective Lipase-Catalysed Acylation of Methyl alpha-D-Glycopyranosides with Fluorinated beta-Lactams




Sundell Riku, Siirola Elina, Kanerva Liisa T

PublisherWiley-VCH Verlag GmbH & Co. KGaA, Weinheim

2014

European Journal of Organic Chemistry

EurJOC

2014

30

6753

6760

8

1434-193X

DOIhttps://doi.org/10.1002/ejoc.201402800



Burkholderia cepacia lipase (lipase PS-D) catalysed acylation with 3,3-difluoro-4-phenyl-, -thiophen-3-yl- and -4-pyridylazetidin-2-ones was examined for the formation of N-Boc-protected 6-O-acylated sugar–β-amino acid conjugates from methyl α-D-galacto-,-gluco- and mannopyranosides and Boc2O. The 6-O-acylated glycopyranoside–β-amino acid conjugates were isolated and characterized. The low solubility of the gluco- and mannopyranosides and the high reactivity of the pyridylazetidinone restricted product formation. Activation of the β-lactam ring by the presence of fluorine substituents was shown to be necessary for the enzymatic acylation reaction. The (S)-enantiomers of the racemic β-lactam substrates reacted with the sugars.




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