Literature DB >> 22304755

Identification of the product of toxoflavin lyase: degradation via a Baeyer-Villiger oxidation.

Benjamin Philmus1, Sameh Abdelwahed, Howard J Williams, Michael K Fenwick, Steven E Ealick, Tadhg P Begley.   

Abstract

Toxoflavin (an azapteridine) is degraded to a single product by toxoflavin lyase (TflA) in a reaction dependent on reductant, Mn(II), and oxygen. The isolated product was fully characterized by NMR and MS and was identified as a triazine in which the pyrimidine ring was oxidatively degraded. A mechanism for toxoflavin degradation based on the identification of the enzymatic product and the recently determined crystal structure of toxoflavin lyase is proposed.

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Year:  2012        PMID： 22304755      PMCID： PMC3332044          DOI： 10.1021/ja211759n

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


  12 in total

1.  BACTERIAL DEGRADATION OF RIBOFLAVIN. V. STOICHIOMETRY OF RIBOFLAVIN DEGRADATION TO OXAMIDE AND OTHER PRODUCTS, OXIDATION OF C14-LABELED INTERMEDIATES AND ISOLATION OF THE PSEUDOMONAD EFFECTING THESE TRANSFORMATIONS.

Authors:  D R HARKNESS; L TSAI; E R STADTMAN
Journal:  Arch Biochem Biophys       Date:  1964-11       Impact factor: 4.013

Review 2.  Integrated Modeling Program, Applied Chemical Theory (IMPACT).

Authors:  Jay L Banks; Hege S Beard; Yixiang Cao; Art E Cho; Wolfgang Damm; Ramy Farid; Anthony K Felts; Thomas A Halgren; Daniel T Mainz; Jon R Maple; Robert Murphy; Dean M Philipp; Matthew P Repasky; Linda Y Zhang; Bruce J Berne; Richard A Friesner; Emilio Gallicchio; Ronald M Levy
Journal:  J Comput Chem       Date:  2005-12       Impact factor: 3.376

3.  A convenient synthesis of toxoflavins, toxoflavin 4-oxides and 1-demethyltoxoflavins.

Authors:  F Yoneda; T Nagamatsu
Journal:  Chem Pharm Bull (Tokyo)       Date:  1975-09       Impact factor: 1.645

4.  Biochemistry: molecular cannibalism.

Authors:  Steven E Ealick; Tadhg P Begley
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

5.  On the origin of the toxicity of toxoflavin.

Authors:  H E LATUASAN; W BERENDS
Journal:  Biochim Biophys Acta       Date:  1961-09-30

6.  BluB cannibalizes flavin to form the lower ligand of vitamin B12.

Authors:  Michiko E Taga; Nicholas A Larsen; Annaleise R Howard-Jones; Christopher T Walsh; Graham C Walker
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

7.  On the biosynthesis of toxoflavin, an azapteridine antibiotic produced by Pseudomonas cocovenenans.

Authors:  B Levenberg; S N Linton
Journal:  J Biol Chem       Date:  1966-02-25       Impact factor: 5.157

8.  Toxoflavin lyase requires a novel 1-His-2-carboxylate facial triad.

Authors:  Michael K Fenwick; Benjamin Philmus; Tadhg P Begley; Steven E Ealick
Journal:  Biochemistry       Date:  2011-01-20       Impact factor: 3.162

9.  Reduction and oxidation of the active site iron in tyrosine hydroxylase: kinetics and specificity.

Authors:  Patrick A Frantom; Javier Seravalli; Stephen W Ragsdale; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2006-02-21       Impact factor: 3.162

10.  Formation of 13C-, 15N-, and 18O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen. Implications for structure and mechanism.

Authors:  Yu Ye; James G Muller; Wenchen Luo; Charles L Mayne; Anthony J Shallop; Roger A Jones; Cynthia J Burrows
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419
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  6 in total

1.  Molecular insight into substrate recognition and catalysis of Baeyer-Villiger monooxygenase MtmOIV, the key frame-modifying enzyme in the biosynthesis of anticancer agent mithramycin.

Authors:  Mary A Bosserman; Theresa Downey; Nicholas Noinaj; Susan K Buchanan; Jürgen Rohr
Journal:  ACS Chem Biol       Date:  2013-09-13       Impact factor: 5.100

Review 2.  The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems.

Authors:  Chia-I Lin; Reid M McCarty; Hung-Wen Liu
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-14       Impact factor: 15.336

3.  Baeyer-Villiger C-C bond cleavage reaction in gilvocarcin and jadomycin biosynthesis.

Authors:  Nidhi Tibrewal; Pallab Pahari; Guojun Wang; Madan K Kharel; Caleb Morris; Theresa Downey; Yanpeng Hou; Tim S Bugni; Jürgen Rohr
Journal:  J Am Chem Soc       Date:  2012-10-29       Impact factor: 15.419

4.  Burkholderia glumae ToxA Is a Dual-Specificity Methyltransferase That Catalyzes the Last Two Steps of Toxoflavin Biosynthesis.

Authors:  Michael K Fenwick; Benjamin Philmus; Tadhg P Begley; Steven E Ealick
Journal:  Biochemistry       Date:  2016-05-03       Impact factor: 3.162

5.  Isolation and characterization of a novel metagenomic enzyme capable of degrading bacterial phytotoxin toxoflavin.

Authors:  Ji-Eun Choi; Cuong Mai Nguyen; Boyoung Lee; Ji Hyun Park; Joon Young Oh; Jung Sup Choi; Jin-Cheol Kim; Jae Kwang Song
Journal:  PLoS One       Date:  2018-01-02       Impact factor: 3.240

6.  Alternative Splicing of the Aflatoxin-Associated Baeyer⁻Villiger Monooxygenase from Aspergillus flavus: Characterisation of MoxY Isoforms.

Authors:  Carmien Tolmie; Martha S Smit; Diederik J Opperman
Journal:  Toxins (Basel)       Date:  2018-12-05       Impact factor: 5.075
  6 in total

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