Literature DB >> 26465651

Natural 1,3-Dipolar Cycloadditions.

Martin Baunach1, Christian Hertweck2,3.   

Abstract

[3+2] in the wild: Biomimetic natural product syntheses and theoretical considerations have indicated that 1,3-dipolar cycloadditions take place in nature. Now, the structure, biosynthesis, and function of a heavily modified prenylated flavin cofactor have been elucidated. In the azomethine ylide form, it undergoes [3+2] cycloadditions with aromatic acids and promotes their decarboxylation.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [3+2] cycloaddition; decarboxylation; flavin coenzyme; prenyl transferase; ubiquinone biosynthesis

Mesh：

Substances：

Year:  2015        PMID： 26465651     DOI： 10.1002/anie.201507120

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

2.  Sterically Shielded, Stabilized Nitrile Imine for Rapid Bioorthogonal Protein Labeling in Live Cells.

Authors:  Peng An; Tracey M Lewandowski; Tuğçe G Erbay; Peng Liu; Qing Lin
Journal:  J Am Chem Soc       Date:  2018-04-02       Impact factor: 15.419

3.  Oxidative Maturation and Structural Characterization of Prenylated FMN Binding by UbiD, a Decarboxylase Involved in Bacterial Ubiquinone Biosynthesis.

Authors:  Stephen A Marshall; Karl Fisher; Aisling Ní Cheallaigh; Mark D White; Karl A P Payne; D A Parker; Stephen E J Rigby; David Leys
Journal:  J Biol Chem       Date:  2017-01-05       Impact factor: 5.157

4.  Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(ii) and copper(ii) complex.

Authors:  Iván Rivilla; Abel de Cózar; Thomas Schäfer; Frank J Hernandez; Alexander M Bittner; Aitziber Eleta-Lopez; Ali Aboudzadeh; José I Santos; José I Miranda; Fernando P Cossío
Journal:  Chem Sci       Date:  2017-08-22       Impact factor: 9.825

Review 5.  The Huisgen Reaction: Milestones of the 1,3-Dipolar Cycloaddition.

Authors:  Martin Breugst; Hans-Ulrich Reissig
Journal:  Angew Chem Int Ed Engl       Date:  2020-05-25       Impact factor: 15.336

6.  The UbiX flavin prenyltransferase reaction mechanism resembles class I terpene cyclase chemistry.

Authors:  Stephen A Marshall; Karl A P Payne; Karl Fisher; Mark D White; Aisling Ní Cheallaigh; Arune Balaikaite; Stephen E J Rigby; David Leys
Journal:  Nat Commun       Date:  2019-05-29       Impact factor: 14.919

7.  Regioselective para-Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase.

Authors:  Stefan E Payer; Stephen A Marshall; Natalie Bärland; Xiang Sheng; Tamara Reiter; Andela Dordic; Georg Steinkellner; Christiane Wuensch; Susann Kaltwasser; Karl Fisher; Stephen E J Rigby; Peter Macheroux; Janet Vonck; Karl Gruber; Kurt Faber; Fahmi Himo; David Leys; Tea Pavkov-Keller; Silvia M Glueck
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-02       Impact factor: 15.336

8.  Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases.

Authors:  Godwin A Aleku; Christoph Prause; Ruth T Bradshaw-Allen; Katharina Plasch; Silvia M Glueck; Samuel S Bailey; Karl A P Payne; David A Parker; Kurt Faber; David Leys
Journal:  ChemCatChem       Date:  2018-07-17       Impact factor: 5.686
  8 in total

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