MilliporeSigma

Squalene-hopene cyclases.

Applied and environmental microbiology (2011-05-03)
Gabriele Siedenburg, Dieter Jendrossek
ABSTRACT

Hopanoids and sterols are members of a large group of cyclic triterpenoic compounds that have important functions in many prokaryotic and eukaryotic organisms. They are biochemically synthesized from linear precursors (squalene, 2,3-oxidosqualene) in only one enzymatic step that is catalyzed by squalene-hopene cyclase (SHC) or oxidosqualene cyclase (OSC). SHCs and OSCs are related in amino acid sequences and probably are derived from a common ancestor. The SHC reaction requires the formation of five ring structures, 13 covalent bonds, and nine stereo centers and therefore is one of the most complex one-step enzymatic reactions. We summarize the knowledge of the properties of triterpene cyclases and details of the reaction mechanism of Alicyclobacillus acidocaldarius SHC. Properties of other SHCs are included.

MATERIALS
Product Number
Brand
Product Description

Supelco
Hop-22(29)-ene solution, 0.1 mg/mL in isooctane, analytical standard
Supelco
Squalene, analytical standard
Sigma-Aldrich
Squalene, ≥98%, liquid