Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Reexamination Certificate
2005-11-15
2008-12-02
Saucier, Sandra E. (Department: 1651)
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
Reexamination Certificate
active
07459301
ABSTRACT:
The present disclosure provides enzymatic methods for generating stereoisomerically pure products by resolving a racemic mixture of N-protected β-lactams with a lipase fromCandida antarcticawith high stereospecificity. The presence of a carbamate protecting group, such as the tert-butoxycarbonyl group protecting group, on the β-lactam enhances enzyme catalysis and stereoselectivity.
REFERENCES:
patent: 6780634 (2004-08-01), Bernegger-Egli
patent: WO 00/03032 (2000-01-01), None
Forro et al., “Lipase-Catalyzed Enantioselective Ring Opening of Unactivated Alicyclic-Fused beta Lactams in an Organic Solvent”, Organic Letters 5 (8) : 1209-1212 (2003), and supporting information.
Supporting information for Forro et al, pp. 1-7 (2003).
International Search Report from PCT/US05/041276, Jul. 12, 2006.
Forro et al., 2004, Direct and Indirect Enzymatic Methods for the Preparation of Enantiopure Cyclic β-Amino Acids and Derivatives from β-Lactams,Mini-Reviews in Organic Chemistry, 1(1):93-102.
Adam et al., 2000, “Synthesis of Optically Active α-Methylene β-Lactams through Lipase-Catalyzed Kinetic Resolution,”Journal of Organic Chemistry, 65(16):4919-4922.
Forro et al., “Vapour-assisted enzymatic hydrolysis of β-lactams in a solvent-free system,” Tetrahedron: Asymmetry, 19:1005-1009 (2008).
McDonnell Boehnen & Hulbert & Berghoff LLP
Rigel Pharmaceuticals Inc.
Saucier Sandra E.
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