Literature DB >> 4368986

Oxaziridines as possible intermediates in flavin monooxygenases.

H W Orf, D Dolphin.   

Abstract

The enzymatic hydroxylation reactions of flavin monooxygenases are suggested to involve an oxaziridine as the active oxygenating agent. The chemistry of these monooxygenases and their nonenzymatic model systems are consistent with an oxaziridine intermediate. Several advantages of the oxaziridine model over the previously proposed "carbonyl oxide" and flavin peroxide models are discussed.

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Year:  1974        PMID: 4368986      PMCID: PMC388523          DOI: 10.1073/pnas.71.7.2646

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN: 0027-8424            Impact factor:   11.205


  11 in total

1.  SALICYLATE HYDROXYLASE, A MONOOXYGENASE REQUIRING FLAVIN ADENINE DINUCLEOTIDE. I. PURIFICATION AND GENERAL PROPERTIES.

Authors:  S YAMAMOTO; M KATAGIRI; H MAENO; O HAYAISHI
Journal:  J Biol Chem       Date:  1965-08       Impact factor: 5.157

2.  Mechanism of action and crystallization of lactic oxidative decarboxylase from Mycobacterium phlei.

Authors:  W B SUTTON
Journal:  J Biol Chem       Date:  1957-05       Impact factor: 5.157

3.  Spectral properties of an oxygenated luciferase-flavin intermediate isolated by low-temperature chromatography.

Authors:  J W Hastings; C Balny; C L Peuch; P Douzou
Journal:  Proc Natl Acad Sci U S A       Date:  1973-12       Impact factor: 11.205

4.  Electronic structures of lumazines and isoalloxazines.

Authors:  J L Fox; S P Laberge; K Nishimoto; L S Forster
Journal:  Biochim Biophys Acta       Date:  1967-04-25

5.  The mechanism of action of the flavoprotein melilotate hydroxylase.

Authors:  S Strickland; V Massey
Journal:  J Biol Chem       Date:  1973-04-25       Impact factor: 5.157

6.  p-Hydroxybenzoate hydroxylase from Pseudomonas fluorescens. Evidence for an oxygenated flavin intermediate.

Authors:  T Spector; V Massey
Journal:  J Biol Chem       Date:  1972-09-10       Impact factor: 5.157

7.  Crystallization and properties of p-hydroxybenzoate hydroxylase from Pseudomonas putida.

Authors:  K Hosokawa; R Y Stanier
Journal:  J Biol Chem       Date:  1966-05-25       Impact factor: 5.157

8.  Nature and mechanisms of oxygenases.

Authors:  O Hayaishi; M Nozaki
Journal:  Science       Date:  1969-04-25       Impact factor: 47.728

9.  Studies on monooxygenases. II. Crystallization and some properties of imidazole acetate monooxygenase.

Authors:  Y Maki; S Yamamoto; M Nozaki; O Hayaishi
Journal:  J Biol Chem       Date:  1969-06-10       Impact factor: 5.157

10.  Crystalline L-lysine oxygenase.

Authors:  H Takeda; O Hayaishi
Journal:  J Biol Chem       Date:  1966-06-10       Impact factor: 5.157

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  5 in total

1.  Biochemical Establishment and Characterization of EncM's Flavin-N5-oxide Cofactor.

Authors:  Robin Teufel; Frederick Stull; Michael J Meehan; Quentin Michaudel; Pieter C Dorrestein; Bruce Palfey; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

Review 2.  Flavin-N5-oxide: A new, catalytic motif in flavoenzymology.

Authors:  Sanjoy Adak; Tadhg P Begley
Journal:  Arch Biochem Biophys       Date:  2017-08-05       Impact factor: 4.013

3.  Nature of the reaction intermediates in the flavin adenine dinucleotide-dependent epoxidation mechanism of styrene monooxygenase.

Authors:  Auric Kantz; George T Gassner
Journal:  Biochemistry       Date:  2010-12-31       Impact factor: 3.162

4.  Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement.

Authors:  Robin Teufel; Akimasa Miyanaga; Quentin Michaudel; Frederick Stull; Gordon Louie; Joseph P Noel; Phil S Baran; Bruce Palfey; Bradley S Moore
Journal:  Nature       Date:  2013-10-27       Impact factor: 49.962

Review 5.  N5 Is the New C4a: Biochemical Functionalization of Reduced Flavins at the N5 Position.

Authors:  Brett A Beaupre; Graham R Moran
Journal:  Front Mol Biosci       Date:  2020-10-30
  5 in total

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