Squalene-hopene Cyclases

Overview

Journal Appl Environ Microbiol

Specialties Environmental Health
Microbiology

Date 2011 May 3

PMID 21531832

Citations 46

Authors

Gabriele Siedenburg

Dieter Jendrossek

Affiliations

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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.

Citing Articles

Structure of Genes Encoding Oxidosqualene Cyclases-Key Enzymes of Triterpenoid Biosynthesis from Sea Cucumber .

Baldaev S, Chausova V, Isaeva K, Boyko A, Stonik V, Isaeva M Int J Mol Sci. 2024; 25(23).

PMID: 39684591 PMC: 11641436. DOI: 10.3390/ijms252312881.

Mining methods and typical structural mechanisms of terpene cyclases.

Huang Z, Ye R, Yu H, Li A, Xu J Bioresour Bioprocess. 2024; 8(1):66.

PMID: 38650244 PMC: 10992375. DOI: 10.1186/s40643-021-00421-2.

Class II terpene cyclases: structures, mechanisms, and engineering.

Pan X, Rudolf J, Dong L Nat Prod Rep. 2023; 41(3):402-433.

PMID: 38105714 PMC: 10954422. DOI: 10.1039/d3np00033h.

OXIDOSQUALENE CYCLASE 1 and 2 influence triterpene biosynthesis and defense in Nicotiana attenuata.

Yang C, Halitschke R, OConnor S Plant Physiol. 2023; 194(4):2580-2599.

PMID: 38101922 PMC: 10980520. DOI: 10.1093/plphys/kiad643.

Computational analysis of carboxylesterase genes and proteins in non-pathogenic food bacterium Alicyclobacillus acidocaldarius: insights from proteogenomics.

Sraphet S, Javadi B World J Microbiol Biotechnol. 2023; 39(12):348.

PMID: 37855845 DOI: 10.1007/s11274-023-03805-y.

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