Mining methods and typical structural mechanisms of terpene cyclases

Abstract

Terpenoids, formed by cyclization and/or permutation of isoprenes, are the most diverse and abundant class of natural products with a broad range of significant functions. One family of the critical enzymes involved in terpenoid biosynthesis is terpene cyclases (TCs), also known as terpene synthases (TSs), which are responsible for forming the ring structure as a backbone of functionally diverse terpenoids. With the recent advances in biotechnology, the researches on terpene cyclases have gradually shifted from the genomic mining of novel enzyme resources to the analysis of their structures and mechanisms. In this review, we summarize both the new methods for genomic mining and the structural mechanisms of some typical terpene cyclases, which are helpful for the discovery, engineering and application of more and new TCs.

Rational reprogramming of the sesquiterpene synthase BcBOT2 yields new terpenes with presilphiperfolane skeleton

“…1A). 19,[33][34][35] Its volume is with 567 Å 3 quite low compared to other sesquiterpene synthase but it exhibits a high druggability score (0.91), which indicates high affinity binding of small "druglike" molecules through the active site. 25,36 The active site pocket is more polar and hydrophilic in the entrance region, while the part further deep inside is mainly composed of nonpolar and hydrophobic amino acids, similar to the active site pocket of other STCs such as TEAS (Fig.…”

Facile Production of (+)-Aristolochene and (+)-Bicyclogermacrene in Escherichia coli Using Newly Discovered Sesquiterpene Synthases from Penicillium expansum

“… The amino acid sequence of Pe TS1 contains the highly conserved motifs of class I TSs, including the aspartate-rich motif 102 DDLLE, the NSE triad 231 NDVYSYEKE, the pyrophosphate sensor 187 R, and the 326 RY pair. The functions of these conserved motifs have been revealed by a number of studies to discover the essential effects on the function of (+)-aristolochene synthase, − which are helpful to well elucidate the structure–function relationship of aristolochene synthases.…”

Heterocyclic and Alkyne Terpenoids by Terpene Synthase‐Mediated Biotransformation of Non‐Natural Prenyl Diphosphates: Access to New Fragrances and Probes

“…The constitution of 5 f was validated by a combination of different NMR spectroscopy methods, including correlation spectroscopy (COSY), heteronuclear multiple-bond correlation spectroscopy (HMBC), and heteronuclear single-quantum correlation spectroscopy (HSQC; Table 2). The key resonances in the corresponding 1 H NMR and HSQC spectra are the two methylene protons H-9Z (δ = 4.83 ppm) and H-9E (δ = 4.78 ppm), as well as the methine proton H-2 (δ = 5.4 ppm) that exhibit a distinct downfield shift. Furthermore, the methyl group at position 7 (δ = 1.65 ppm) is crucial.…”

“…chemnetbase.com). [1] They act as attractants, toxins, repellants, or antibiotics among other biological activities. [2] Volatile monoand sesquiterpenes are the main constituents of flower scents and natural aromas.…”

“…Terpenoids constitute one of the largest classes of secondary metabolites comprising more than 80000 compounds, many of which have high biological and pharmaceutical importance as reported in the Dictionary of Natural Products ( http://dnp.chemnetbase.com ). [1] They act as attractants, toxins, repellants, or antibiotics among other biological activities. [2] Volatile mono‐ and sesquiterpenes are the main constituents of flower scents and natural aromas.…”