Structural and chemical biology of terpenoid cyclases

DW Christianson - Chemical reviews, 2017 - ACS Publications
The year 2017 marks the twentieth anniversary of terpenoid cyclase structural biology: a trio
of terpenoid cyclase structures reported together in 1997 were the first to set the foundation …

Sesquiterpene synthases: passive catalysts or active players?

DJ Miller, RK Allemann - Natural Product Reports, 2012 - pubs.rsc.org
Covering: up to July 2011 Sesquiterpene synthases catalyse the metal dependent turnover
of farnesyl diphosphate to generate a class of natural products characterised by an …

Germacrene A–A central intermediate in sesquiterpene biosynthesis

H Xu, JS Dickschat - Chemistry–A European Journal, 2020 - Wiley Online Library
This review summarises known sesquiterpenes whose biosyntheses proceed through the
intermediate germacrene A. First, the occurrence and biosynthesis of germacrene A in …

Mechanistic insights from the binding of substrate and carbocation intermediate analogues to aristolochene synthase

M Chen, N Al-Lami, M Janvier, EL D'Antonio… - Biochemistry, 2013 - ACS Publications
Aristolochene synthase, a metal-dependent sesquiterpene cyclase from Aspergillus terreus,
catalyzes the ionization-dependent cyclization of farnesyl diphosphate (FPP) to form the …

Probing eudesmane cation− π interactions in catalysis by aristolochene synthase with non-canonical amino acids

JA Faraldos, AK Antonczak, V González… - Journal of the …, 2011 - ACS Publications
Stabilization of the reaction intermediate eudesmane cation (3) through interaction with Trp
334 during catalysis by aristolochene synthase from Penicillium roqueforti was investigated …

A 1, 6-ring closure mechanism for (+)-δ-cadinene synthase?

JA Faraldos, DJ Miller, V Gonzalez… - Journal of the …, 2012 - ACS Publications
Recombinant (+)-δ-cadinene synthase (DCS) from Gossypium arboreum catalyzes the metal-
dependent cyclization of (E, E)-farnesyl diphosphate (FDP) to the cadinane sesquiterpene δ …

Sesquiterpene synthase‐catalysed formation of a new medium‐sized cyclic terpenoid ether from farnesyl diphosphate analogues

F Huynh, DJ Grundy, RL Jenkins, DJ Miller… - …, 2018 - Wiley Online Library
Terpene synthases catalyse the first step in the conversion of prenyl diphosphates to
terpenoids. They act as templates for their substrates to generate a reactive conformation …

[HTML][HTML] Comparative analysis and validation of the malachite green assay for the high throughput biochemical characterization of terpene synthases

M Vardakou, M Salmon, JA Faraldos, PE O'Maille - MethodsX, 2014 - Elsevier
Terpenes are the largest group of natural products with important and diverse biological
roles, while of tremendous economic value as fragrances, flavours and pharmaceutical …

Chemoenzymatic preparation of germacrene analogues

O Cascón, S Touchet, DJ Miller, V Gonzalez… - Chemical …, 2012 - pubs.rsc.org
A small library of novel germacrenes was generated using a combination of two plant
enzymes, germacrene A synthase, and D synthase and modified farnesyl diphosphate …

Primary amine, thiourea-based dual catalysis motif for synthesis of stereogenic, all-carbon quaternary center-containing cycloalkanones

JY Kang, RG Carter - Organic letters, 2012 - ACS Publications
The enantioselective synthesis of α, α-disubstituted cycloalkanones has been developed
using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and …