55154-48-8Relevant articles and documents
Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin
Venkataiah, Mallam,Reddipalli, Gowrisankar,Jasti, Lakshmi Swarnalatha,Fadnavis, Nitin W.
experimental part, p. 1855 - 1860 (2012/01/13)
The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).
Microwave synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas Aeruginosa
Oliver, Colin M.,Schaefer, Amy L.,Greenberg, E. Peter,Sufrin, Janice R.
experimental part, p. 1559 - 1575 (2010/02/16)
The bacterial quorum sensing (QS) signal molecule 3-oxo-dodecanoyl-L- homoserine lactone (OdDHL) is produced by the opportunistic pathogen Pseudomonas aeruginosa and controls expression of virulence factors associated with life threatening infections in i
Method for synthesizing oxazinones
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Page 10, (2010/02/06)
New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.
