Literature DB >> 10814381

Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis.

M M Ravn1, R M Coates, J E Flory, R J Peters, R Croteau.   

Abstract

[reaction: see text] Syntheses and enzymatic cyclizations of 8alpha-hydroxy-17-nor copalyl diphosphate (8a), (15R)-[15-2H1] 8b, and (15R,17E)-[15-3H1,17-2H1] copalyl diphosphate ([2H,3H] 2) catalyzed by recombinant abietadiene synthase (rAS) gave 17-nor manoyl oxide (9a), (16E)-[16-2H1] 9b, and (15S,16R)-[16-2H1,16-3H1] abietadiene ([2H1,3H1] 4), respectively. These and other results indicate that conversion of CPP (2) to abietadiene (4) occurs by anti S(N)' cyclization to a sandaracopimar-15-en-8-yl carbocation intermediate (13+, 13beta-methyl) followed by hydrogen transfer and methyl migration suprafacially on the si face of the vinyl group.

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Year:  2000        PMID： 10814381     DOI： 10.1021/ol991230p

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  17 in total

Review 1.  Molecular scaffolds for chemical wizardry: learning nature's rules for terpene cyclases.

Authors:  B Greenhagen; J Chappell
Journal:  Proc Natl Acad Sci U S A       Date:  2001-11-20       Impact factor: 11.205

2.  Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control.

Authors:  Effendi Leonard; Parayil Kumaran Ajikumar; Kelly Thayer; Wen-Hai Xiao; Jeffrey D Mo; Bruce Tidor; Gregory Stephanopoulos; Kristala L J Prather
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-19       Impact factor: 11.205

3.  Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement.

Authors:  Reuben J Peters; Rodney B Croteau
Journal:  Proc Natl Acad Sci U S A       Date:  2002-01-22       Impact factor: 11.205

4.  A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes.

Authors:  Vasiliki Falara; Eran Pichersky; Angelos K Kanellis
Journal:  Plant Physiol       Date:  2010-07-01       Impact factor: 8.340

5.  Insights into diterpene cyclization from structure of bifunctional abietadiene synthase from Abies grandis.

Authors:  Ke Zhou; Yang Gao; Julie A Hoy; Francis M Mann; Richard B Honzatko; Reuben J Peters
Journal:  J Biol Chem       Date:  2012-01-04       Impact factor: 5.157

Review 6.  Structural and Chemical Biology of Terpenoid Cyclases.

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

Review 7.  Terpenoid synthase structures: a so far incomplete view of complex catalysis.

Authors:  Yang Gao; Richard B Honzatko; Reuben J Peters
Journal:  Nat Prod Rep       Date:  2012-08-21       Impact factor: 13.423

8.  Functional characterization of nine Norway Spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily.

Authors:  Diane M Martin; Jenny Fäldt; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2004-08-13       Impact factor: 8.340

9.  Synthetic efficiency in enzyme mechanisms involving carbocations: aristolochene synthase.

Authors:  Rudolf K Allemann; Neil J Young; Shuhua Ma; Donald G Truhlar; Jiali Gao
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

10.  A functional genomics approach to tanshinone biosynthesis provides stereochemical insights.

Authors:  Wei Gao; Matthew L Hillwig; Luqi Huang; Guanghong Cui; Xueyong Wang; Jianqiang Kong; Bin Yang; Reuben J Peters
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005
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