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US 7,459,301 B2Granted
Stereoisomerically enriched N-protected β-lactams using candida antarctica
AssigneeRigel Pharmaceuticals, Inc.
InventorAnkush Argade
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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 from Candida antarctica with 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.
Claims13
A method for generating a stereoisomerically pure N-protected β-lactam from a mixture of diastereomers, comprising contacting an N-protected β-lactam mixture comprising enantiomers according to structural formulae (1) and (2):
- wherein:
- A represents a saturated or unsaturated, monocyclic, polycyclic or bridged polycyclic ring;
- and
- R is a carbamate or thiocarbamate protecting group,
- with a lipase from Candida antarctica under conditions in which the lipase selectively cleaves enantiomer 2, thereby yielding a mixture of reaction products according to structural formulae 1 and 4:
2 more elements
Dependencies are inferred from the claim text.