Journal
TETRAHEDRON
Volume 60, Issue 3, Pages 711-716Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2003.11.064
Keywords
beta-lactamase; signature amidase; Sulfolobus solfataricus; biotransformations
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The resolution of the bicyclic synthon (rac)-gamma-lactam (2-azabicyclo[2.2.1]hept-5-en-3-one) is an important step in the synthesis of a group of chemotherapuetic agents known as carbocyclic nucleosides. The archaeon Sulfolobus solfataricus MT4 produces a thermostable gamma-lactamase that has a high sequence homology to the signature amidase family of enzymes. It shows similar inhibition patterns of amidases towards benzonitrile, phenylmethylsulfonyl fluoride and heavy metals such as Hg2+, and is activated by thiol reagents. The enzyme selectively cleaves the (+)-enantiomer from a racemic mix of gamma-lactam. It also exhibits general amidase activity by cleaving linear and branched aliphatic and aromatic amides. The enzyme catalyses the synthesis of benzoic hydrazide from benzamide preferentially to benzamide cleavage in the presence of excess hydrazine. This enzyme has potential for use in industrial biotransformations in the production of both carbocyclic nucleosides and hydrazides. (C) 2003 Published by Elsevier Ltd.
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