Literature DB >> 12121093

Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis.

Mitchell L Wise1, Marek Urbansky, Gregory L Helms, Robert M Coates, Rodney Croteau.   

Abstract

Regiospecifically labeled geranyl diphosphates ((2E,6E)-[1,1,8,8,8-(2)H(5)]- and (2E,6Z)-[1,1,9,9,9-(2)H(5)]-GDP) and D(2)O incorporation, in concert with NMR spectrometry, were employed to demonstrate a unique intramolecular syn-facial protonation-cyclization mechanism of action of 1,8-cineole synthase.

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Year:  2002        PMID： 12121093     DOI： 10.1021/ja0265714

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

1.  Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation.

Authors:  Shu-Shan Gao; Marc Garcia-Borràs; Joyann S Barber; Yang Hai; Abing Duan; Neil K Garg; K N Houk; Yi Tang
Journal:  J Am Chem Soc       Date:  2017-03-01       Impact factor: 15.419

2.  The α-Terpineol to 1,8-Cineole Cyclization Reaction of Tobacco Terpene Synthases.

Authors:  Birgit Piechulla; Richard Bartelt; Anne Brosemann; Uta Effmert; Harro Bouwmeester; Frank Hippauf; Wolfgang Brandt
Journal:  Plant Physiol       Date:  2016-10-11       Impact factor: 8.340

3.  A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus.

Authors:  Jan Rinkel; Patrick Rabe; Laura Zur Horst; Jeroen S Dickschat
Journal:  Beilstein J Org Chem       Date:  2016-11-04       Impact factor: 2.883

4.  Taming the Reactivity of Monoterpene Synthases To Guide Regioselective Product Hydroxylation.

Authors:  Nicole G H Leferink; Kara E Ranaghan; Jaime Battye; Linus O Johannissen; Sam Hay; Marc W van der Kamp; Adrian J Mulholland; Nigel S Scrutton
Journal:  Chembiochem       Date:  2019-12-03       Impact factor: 3.164

Review 5.  Germacrene A-A Central Intermediate in Sesquiterpene Biosynthesis.

Authors:  Houchao Xu; Jeroen S Dickschat
Journal:  Chemistry       Date:  2020-09-30       Impact factor: 5.236

Review 6.  Predictive Engineering of Class I Terpene Synthases Using Experimental and Computational Approaches.

Authors:  Nicole G H Leferink; Nigel S Scrutton
Journal:  Chembiochem       Date:  2021-11-03       Impact factor: 3.461

7.  Structural Basis of Catalysis in the Bacterial Monoterpene Synthases Linalool Synthase and 1,8-Cineole Synthase.

Authors:  Vijaykumar Karuppiah; Kara E Ranaghan; Nicole G H Leferink; Linus O Johannissen; Muralidharan Shanmugam; Aisling Ní Cheallaigh; Nathan J Bennett; Lewis J Kearsey; Eriko Takano; John M Gardiner; Marc W van der Kamp; Sam Hay; Adrian J Mulholland; David Leys; Nigel S Scrutton
Journal:  ACS Catal       Date:  2017-08-09       Impact factor: 13.084
  7 in total

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