Literature DB >> 29969566

Synthesis of 8-Hydroxygeraniol.

Francesca M Ippoliti1, Joyann S Barber1, Yi Tang1, Neil K Garg1.   

Abstract

An operationally simple protocol for the conversion of geranyl acetate to 8-hydroxygeraniol is reported. The convenient two-step procedure relies on an efficient, chemo- and regioselective SeO2-promoted oxidation, followed by straightforward deacetylation. This facile means to prepare 8-hydroxygeraniol is expected to enable biosynthetic studies pertaining to thousands of monoterpene indole alkaloids.

Entities:  

Mesh:

Substances:

Year:  2018        PMID: 29969566      PMCID: PMC6508077          DOI: 10.1021/acs.joc.8b01544

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  15 in total

Review 1.  Metabolic engineering for the production of natural products.

Authors:  Lauren B Pickens; Yi Tang; Yit-Heng Chooi
Journal:  Annu Rev Chem Biomol Eng       Date:  2011       Impact factor: 11.059

2.  S-Adenosyl-L-methionine: loganic acid methyltransferase. A carboxyl-alkylating enzyme from Vinca rosea.

Authors:  K M Madyastha; R Guarnaccia; C Baxter; C J Coscia
Journal:  J Biol Chem       Date:  1973-04-10       Impact factor: 5.157

3.  Engineering of a Nepetalactol-Producing Platform Strain of Saccharomyces cerevisiae for the Production of Plant Seco-Iridoids.

Authors:  Alex Campbell; Philippe Bauchart; Nicholas D Gold; Yun Zhu; Vincenzo De Luca; Vincent J J Martin
Journal:  ACS Synth Biol       Date:  2016-03-25       Impact factor: 5.110

4.  Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase.

Authors:  S Irmler; G Schröder; B St-Pierre; N P Crouch; M Hotze; J Schmidt; D Strack; U Matern; J Schröder
Journal:  Plant J       Date:  2000-12       Impact factor: 6.417

5.  Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols.

Authors:  H Ikeda; N Esaki; S Nakai; K Hashimoto; S Uesato; K Soda; T Fujita
Journal:  J Biochem       Date:  1991-02       Impact factor: 3.387

6.  De novo production of the plant-derived alkaloid strictosidine in yeast.

Authors:  Stephanie Brown; Marc Clastre; Vincent Courdavault; Sarah E O'Connor
Journal:  Proc Natl Acad Sci U S A       Date:  2015-02-09       Impact factor: 11.205

7.  Strategies for engineering plant natural products: the iridoid-derived monoterpene indole alkaloids of Catharanthus roseus.

Authors:  Sarah E O'Connor
Journal:  Methods Enzymol       Date:  2012       Impact factor: 1.682

8.  Characterization of 10-hydroxygeraniol dehydrogenase from Catharanthus roseus reveals cascaded enzymatic activity in iridoid biosynthesis.

Authors:  Ramakrishnan Krithika; Prabhakar Lal Srivastava; Bajaj Rani; Swati P Kolet; Manojkumar Chopade; Mantri Soniya; Hirekodathakallu V Thulasiram
Journal:  Sci Rep       Date:  2015-02-05       Impact factor: 4.379

9.  An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.

Authors:  Fernando Geu-Flores; Nathaniel H Sherden; Vincent Courdavault; Vincent Burlat; Weslee S Glenn; Cen Wu; Ezekiel Nims; Yuehua Cui; Sarah E O'Connor
Journal:  Nature       Date:  2012-11-21       Impact factor: 69.504

10.  Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX.

Authors:  Anna M Bogazkaya; Clemens J von Bühler; Sebastian Kriening; Alexandrine Busch; Alexander Seifert; Jürgen Pleiss; Sabine Laschat; Vlada B Urlacher
Journal:  Beilstein J Org Chem       Date:  2014-06-13       Impact factor: 2.883

View more
  2 in total

1.  Production of semi-biosynthetic nepetalactone in yeast.

Authors:  John M Billingsley; Jose L Anguiano; Yi Tang
Journal:  J Ind Microbiol Biotechnol       Date:  2019-06-05       Impact factor: 3.346

2.  Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis.

Authors:  Tabitha T Schempp; Michael J Krische
Journal:  J Am Chem Soc       Date:  2022-01-10       Impact factor: 15.419

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.