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Scope, limitations and classification of lactamases.

Zeinab Assaf1, Kurt Faber2, Mélanie Hall2

  • 1Austrian Center of Industrial Biotechnology, c/o, Austria; Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.

Journal of Biotechnology
|April 6, 2016
PubMed
Summary

Enzymes called lactamases can break down cyclic amides (lactams). Researchers identified specific lactamases for γ- and δ-lactams, revealing structural differences between enzymes that process (+)- and (-)-lactams.

Keywords:
AmidaseEnantioselectiveEnzymeHydrolysisKinetic resolutionLactamaseVince lactam

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Area of Science:

  • Biochemistry
  • Enzymology
  • Organic Chemistry

Background:

  • Amide bond hydrolysis is crucial in biological systems, with amidases and peptidases acting on linear amides.
  • Cyclic amides (lactams) generally resist hydrolysis by proteases, requiring specialized lactamases.
  • While β-lactamases are well-studied, enzymes for less reactive γ- and δ-lactams are rare due to low ring strain.

Purpose of the Study:

  • To investigate enzymatic hydrolysis of less reactive 5- and 6-membered ring lactams.
  • To identify and characterize enantioselective biocatalysts for lactam hydrolysis.
  • To correlate enzyme structure and amino acid sequence with stereoselectivity.

Main Methods:

  • Enzyme screening for lactamase activity.
  • Identification of specific substrates like (±)-2-azabicyclo[2.2.1]hept-5-en-3-one (rac-Vince lactam).
  • Analysis of amino acid sequences and protein structures of identified lactamases.

Main Results:

  • Discovery of enantiocomplementary biocatalysts for rac-Vince lactam and derivatives.
  • (+)-Lactamases identified within the amidase signature family (Ser-Ser-Lys triad).
  • (-)-Lactamase activity found in α/β-hydrolase fold family enzymes (Ser-His-Asp triad).

Conclusions:

  • Enzyme structure and sequence dictate stereochemical preference in lactam hydrolysis.
  • Distinct catalytic triads (Ser-Ser-Lys vs. Ser-His-Asp) correlate with enantioselectivity.
  • Understanding these enzymes aids in developing biocatalysts for industrially relevant lactams.