Jul 2026· Journal of Physical Chemistry B· Vol 130, pp. 7780-7790· 0 citations· 44 references
Medicine
TL;DR
It is revealed that cyclization and quenching are governed by distinct active site residues, providing a rational strategy for the functional reshaping of triterpene synthases with customized product profiles.
Abstract
The triterpene synthase AaOSC-22030 from Artemisia argyi exhibits remarkable catalytic promiscuity, converting 2,3-oxidosqualene into diverse triterpenoid skeletons. In this study, we employed multiscale molecular dynamics, static QM/MM calculations, and site-directed mutagenesis to elucidate the origins of this diversity. Our analysis identifies residue 728 as a pivotal determinant. We reveal that the substitution of a conserved aromatic residue with a polar serine (S728) creates a relaxed steric environment, permitting broad conformational exploration, while simultaneously serving as a general base to intercept intermediates. Strikingly, the S728Y mutation transformed the promiscuous enzyme into a specific synthase, yielding Dammarendiol II as the exclusive product. Furthermore, the E371A mutant demonstrated that the N369/E371 dyad independently controls the terminal hydration of pentacyclic products. These findings highlight that cyclization and quenching are governed by distinct active site residues, providing a rational strategy for the functional reshaping of triterpene synthases with customized product profiles.
Oxidosqualene cyclases (OSCs) convert linear 2,3-oxidosqualene into diverse polycyclic triterpenoids. The precise control over highly reactive carbocation intermediates, particularly the ultimate quenching mechanism (deprotonation vs hydroxylation), remains a fundamental challenge in mechanism-driven enzyme reshaping...
Chen-Xu Liu, Shun Liang, Ying Zheng et al.· Journal of Chemical Theory a...· 0 citations
Sesquiterpene synthases generate diverse terpenoid skeletons through carbocation-driven cyclization cascades. Here, we performed a comparative mechanistic study of Artemisia argyisesquiterpene synthase (AaCPS) and Zingiber zerumbet synthase 1 (ZSS1), which exhibit reversed major-product profiles. GC–MS analysis showe...
A substrate mimic strategy using taxadien-2-one (taxadienone), which is selectively epoxidized by CYP725A4 at the C4=C5 double bond, suggests epoxidation as its major catalytic pathway, and provides crucial insights into CYP725A4 catalytic promiscuity.
Enzyme engineering serves as a powerful tool in biocatalysis, enabling the development of enzymes with improved stability, activity, and specificity for a range of academic, industrial, and pharmaceutical applications. However, a limited understanding of sequence–structure–function relationships in terpene synthases, t...
The difructose dianhydride I synthase/hydrolase α FFase 1 catalyzes the reversible transformation of inulobiose into difructose dianhydride I, a component of caramel. The proposed reaction mechanism of such a transformation consists of a glycosylation step followed by a cyclization to yield the dianhydride from the dis...
Santiago Alonso-Gil, Bruno Di Geronimo, T. Kashima et al.· Chemistry· 0 citations
Terpene cyclases (TCs) typically transform acyclic oligoprenyl pyrophosphates through carbocationic cyclization cascades. However, recently discovered bacterial pathways generate compact, cyclized and stereochemically defined noncanonical intermediates through methyltransferases prior to TC catalysis, raising the que...
Ke-Xin Yang, M. Groll, Jeroen S. Dickschat· Journal of the American Chem...· 0 citations
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