Literature DB >> 20442917

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

Dean J Tantillo1.   

Abstract

In this tutorial review, structures encountered in carbocation cascade polycyclization reactions leading to terpene natural products are surveyed. The nature of delocalization in these carbocations is discussed in detail. For select cases, the ability of functional groups in enzyme active sites to modulate this delocalization is discussed. In addition to carbocation intermediates, cationic transition state structures are also described.

Entities:  

Mesh:

Substances:

Year:  2010        PMID: 20442917     DOI: 10.1039/b917107j

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  29 in total

1.  Biomimetic Platinum-Promoted Polyene Polycyclizations: Influence of Alkene Substitution and Pre-cyclization Conformations.

Authors:  Christina H McCulley; Michael J Geier; Brandi M Hudson; Michel R Gagné; Dean J Tantillo
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  Chemoselective conversion of biologically sourced polyols into chiral synthons.

Authors:  Laura L Adduci; Trandon A Bender; Jennifer A Dabrowski; Michel R Gagné
Journal:  Nat Chem       Date:  2015-07       Impact factor: 24.427

3.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

4.  Biosynthetic consequences of multiple sequential post-transition-state bifurcations.

Authors:  Young Joo Hong; Dean J Tantillo
Journal:  Nat Chem       Date:  2014-01-19       Impact factor: 24.427

5.  Catalytic Plasticity of Germacrene A Oxidase Underlies Sesquiterpene Lactone Diversification.

Authors:  Trinh-Don Nguyen; Moonhyuk Kwon; Soo-Un Kim; Conrad Fischer; Dae-Kyun Ro
Journal:  Plant Physiol       Date:  2019-09-18       Impact factor: 8.340

6.  Terminating platinum-initiated cation-olefin reactions with simple alkenes.

Authors:  Joseph G Sokol; Chandra Sekhar Korapala; Peter S White; Jennifer J Becker; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-13       Impact factor: 15.336

7.  Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase.

Authors:  Sibongile Mafu; Prema Sambandaswami Karunanithi; Teresa Ann Palazzo; Bronwyn Lee Harrod; Selina Marakana Rodriguez; Iris Natalie Mollhoff; Terrence Edward O'Brien; Shen Tong; Oliver Fiehn; Dean J Tantillo; Jörg Bohlmann; Philipp Zerbe
Journal:  Proc Natl Acad Sci U S A       Date:  2017-01-17       Impact factor: 11.205

Review 8.  Structural and Chemical Biology of Terpenoid Cyclases.

Authors:  David W Christianson
Journal:  Chem Rev       Date:  2017-08-25       Impact factor: 60.622

9.  Structure of 2-methylisoborneol synthase from Streptomyces coelicolor and implications for the cyclization of a noncanonical C-methylated monoterpenoid substrate.

Authors:  Mustafa Köksal; Wayne K W Chou; David E Cane; David W Christianson
Journal:  Biochemistry       Date:  2012-03-28       Impact factor: 3.162

10.  Plasticity and evolution of (+)-3-carene synthase and (-)-sabinene synthase functions of a sitka spruce monoterpene synthase gene family associated with weevil resistance.

Authors:  Christopher R Roach; Dawn E Hall; Philipp Zerbe; Jörg Bohlmann
Journal:  J Biol Chem       Date:  2014-07-11       Impact factor: 5.157

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.