Regio- and Stereoselective Lipase-Catalysed Acylation of Methyl α- D-Glycopyranosides with Fluorinated β-Lactams.
- Resource Type
- Article
- Authors
- Sundell, Riku; Siirola, Elina; Kanerva, Liisa T.
- Source
- European Journal of Organic Chemistry. Oct2014, Vol. 2014 Issue 30, p6753-6760. 8p.
- Subject
- *CHEMICAL synthesis
*LACTAMS
*ACYLATION
*CATALYSIS research
*LIPASES
*STEREOSELECTIVE reactions
*FLUORINE compounds
*AMINO acids
- Language
- ISSN
- 1434-193X
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. [ABSTRACT FROM AUTHOR]