Biosynthesis via carbocations: theoretical studies on terpene formation

DJ Tantillo - Natural product reports, 2011 - pubs.rsc.org
Biosynthesis via carbocations: Theoretical studies on terpene formation - Natural Product Reports
(RSC Publishing) DOI:10.1039/C1NP00006C Royal Society of Chemistry View PDF …

The carbocation continuum in terpene biosynthesis—where are the secondary cations?

DJ Tantillo - Chemical Society Reviews, 2010 - pubs.rsc.org
In this tutorial review, structures encountered in carbocation cascade polycyclization
reactions leading to terpene natural products are surveyed. The nature of delocalization in …

Sesquiterpene Synthase from the Botrydial Biosynthetic Gene Cluster of the Phytopathogen Botrytis cinerea

C Pinedo, CM Wang, JM Pradier, B Dalmais… - ACS chemical …, 2008 - ACS Publications
The fungus Botrytis cinerea is the causal agent of the economically important gray mold
disease that affects more than 200 ornamental and agriculturally important plant species. B …

Four-step access to the sesquiterpene natural product presilphiperfolan-1β-ol and unnatural derivatives via supramolecular catalysis

LD Syntrivanis, I Némethová, D Schmid… - Journal of the …, 2020 - ACS Publications
Terpenes constitute one of the most structurally varied classes of natural products. A wide
range of these structures are produced in nature by type I terpene cyclase enzymes from …

A potential energy surface bifurcation in terpene biosynthesis

YJ Hong, DJ Tantillo - Nature chemistry, 2009 - nature.com
Terpenes comprise a class of natural products that includes molecules with thousands of
distinct structurally and stereochemically complex molecular architectures. The core …

Consequences of conformational preorganization in sesquiterpene biosynthesis: theoretical studies on the formation of the bisabolene, curcumene, acoradiene …

YJ Hong, DJ Tantillo - Journal of the American Chemical Society, 2009 - ACS Publications
Quantum chemical calculations on cyclization mechanisms for several sesquiterpene
families proposed to be closely related to each other in a biogenic sense (the bisabolene …

Challenges posed to bornyl diphosphate synthase: diverging reaction mechanisms in monoterpenes

M Weitman, DT Major - Journal of the American Chemical Society, 2010 - ACS Publications
The simplest form of terpenoid chemistry is found for the monoterpenes, which give plants
fragrance, flavor, and medicinal properties. Monoterpene synthases employ geranyl …

Biosynthesis of the Sesquiterpene Botrydial in Botrytis cinerea. Mechanism and Stereochemistry of the Enzymatic Formation of Presilphiperfolan-8β-ol

CM Wang, R Hopson, X Lin… - Journal of the American …, 2009 - ACS Publications
Presilphiperfolan-8β-ol synthase, encoded by the BcBOT2 gene from the necrotrophic plant
pathogen Botrytis cinerea, catalyzes the multistep cyclization of farnesyl diphosphate (2) to …

How cyclobutanes are assembled in nature–insights from quantum chemistry

YJ Hong, DJ Tantillo - Chemical Society Reviews, 2014 - pubs.rsc.org
Biosynthetic production of cyclobutanes leads to many complex natural products. Recently,
theoretical work employing quantum chemical calculations has shed light on many of the …

Mechanistic Similarities of Sesquiterpene Cyclases PenA, Omp6/7, and BcBOT2 Are Unraveled by an Unnatural “FPP-Ether” Derivative

V Harms, V Ravkina, A Kirschning - Organic Letters, 2021 - ACS Publications
The sesquiterpene cyclases pentalenene synthase (PenA) and two Δ6-protoilludene
synthases Omp6 and Omp7 convert a FPP ether into several new tetrahydrofurano …