Squalene-hopene cyclase

From Proteopedia

Function

Squalene-hopene cyclase or oxidosqualene cyclase (SHC) catalyzes the conversion of acyclic squalene into the pentacyclic hopene and hopanol in prokaryotes. The reaction which SHC cactalyzes involves the breaking or forming of 13 covalent bonds, the formation of 9 chiral centers and the formation of 5 rings in a single step^[1].

Relevance

The hopenoids condense lipid membranes and reduce their permeability.

Structural highlights

The active site of SHC binds the close substrate analog azosqualene^[2]. Water molecules are shown as red spheres.

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Structure of squalene-hopene cyclase complex with 2-azasqualene and detergent (PDB code 1ump).

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3D structures of squalene-hopene cyclase

Updated on 09-November-2020

Squalene-hopene cyclase

Squalene-hopene cyclase complexes

References

↑ Hammer SC, Marjanovic A, Dominicus JM, Nestl BM, Hauer B. Squalene hopene cyclases are protonases for stereoselective Bronsted acid catalysis. Nat Chem Biol. 2015 Feb;11(2):121-6. doi: 10.1038/nchembio.1719. Epub 2014 Dec, 15. PMID:25503928 doi:http://dx.doi.org/10.1038/nchembio.1719
↑ Reinert DJ, Balliano G, Schulz GE. Conversion of squalene to the pentacarbocyclic hopene. Chem Biol. 2004 Jan;11(1):121-6. PMID:15113001 doi:http://dx.doi.org/10.1016/j.chembiol.2003.12.013