Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A Remarkable Oxidative Cascade That Replaces the Riboflavin C8 Methyl with an Amino Group during Roseoflavin Biosynthesis.

Literature DB >> 27331868

A Remarkable Oxidative Cascade That Replaces the Riboflavin C8 Methyl with an Amino Group during Roseoflavin Biosynthesis.

Isita Jhulki¹, Prem K Chanani¹, Sameh H Abdelwahed¹, Tadhg P Begley¹.

Abstract

Roseoflavin is a naturally occurring riboflavin analogue with antibiotic properties. It is biosynthesized from riboflavin in a reaction involving replacement of the C8 methyl with a dimethylamino group. Herein we report the identification of a flavin-dependent enzyme that converts flavin mononucleotide (FMN) and glutamate to 8-amino-FMN via the intermediacy of 8-formyl-FMN. A mechanistic proposal for this remarkable transformation is proposed.

Entities: CellLine Chemical Disease Species

Mesh：

Substances：

Year: 2016 PMID： 27331868 PMCID： PMC5610575 DOI： 10.1021/jacs.6b02469

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

19 in total

Review 1. Oxidative cascades: a facile biosynthetic strategy for the assembly of complex molecules.

Authors: Pieter Dorrestein; Tadhg P Begley
Journal: Bioorg Chem Date: 2005-06 Impact factor: 5.275

2. Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process.

Authors: Jianfeng Jin; Hortense Mazon; Robert H H van den Heuvel; Albert J Heck; Dick B Janssen; Marco W Fraaije
Journal: FEBS J Date: 2008-09-11 Impact factor: 5.542

Review 3. Natural riboflavin analogs.

Authors: Danielle Biscaro Pedrolli; Frank Jankowitsch; Julia Schwarz; Simone Langer; Shinobu Nakanishi; Matthias Mack
Journal: Methods Mol Biol Date: 2014

4. Thiamin biosynthesis in eukaryotes: characterization of the enzyme-bound product of thiazole synthase from Saccharomyces cerevisiae and its implications in thiazole biosynthesis.

Authors: Abhishek Chatterjee; Christopher T Jurgenson; Frank C Schroeder; Steven E Ealick; Tadhg P Begley
Journal: J Am Chem Soc Date: 2006-06-07 Impact factor: 15.419

5. Riboflavin-overproducing strains of Lactobacillus fermentum for riboflavin-enriched bread.

Authors: Pasquale Russo; Vittorio Capozzi; Mattia Pia Arena; Giuseppina Spadaccino; María Teresa Dueñas; Paloma López; Daniela Fiocco; Giuseppe Spano
Journal: Appl Microbiol Biotechnol Date: 2014-01-12 Impact factor: 4.813

6. Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.

Authors: Lori A Maggio-Hall; Pieter C Dorrestein; Jorge C Escalante-Semerena; Tadhg P Begley
Journal: Org Lett Date: 2003-06-26 Impact factor: 6.005

7. Formation of roseoflavin from guanine through riboflavin.

Authors: K Matsui; N Juri; Y Kubo; S Kasai
Journal: J Biochem Date: 1979-07 Impact factor: 3.387

8. Roseoflavin is a natural antibacterial compound that binds to FMN riboswitches and regulates gene expression.

Authors: Elaine R Lee; Kenneth F Blount; Ronald R Breaker
Journal: RNA Biol Date: 2009-04-30 Impact factor: 4.652

9. Saccharomyces cerevisiae THI4p is a suicide thiamine thiazole synthase.

Authors: Abhishek Chatterjee; N Dinuka Abeydeera; Shridhar Bale; Pei-Jing Pai; Pieter C Dorrestein; David H Russell; Steven E Ealick; Tadhg P Begley
Journal: Nature Date: 2011-10-26 Impact factor: 49.962

10. Structural and kinetic studies on RosA, the enzyme catalysing the methylation of 8-demethyl-8-amino-d-riboflavin to the antibiotic roseoflavin.

Authors: Chanakan Tongsook; Michael K Uhl; Frank Jankowitsch; Matthias Mack; Karl Gruber; Peter Macheroux
Journal: FEBS J Date: 2016-03-17 Impact factor: 5.542

5 in total

A Remarkable Oxidative Cascade That Replaces the Riboflavin C8 Methyl with an Amino Group during Roseoflavin Biosynthesis.

Review 1. Oxidative cascades: a facile biosynthetic strategy for the assembly of complex molecules.

2. Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process.

Review 3. Natural riboflavin analogs.

4. Thiamin biosynthesis in eukaryotes: characterization of the enzyme-bound product of thiazole synthase from Saccharomyces cerevisiae and its implications in thiazole biosynthesis.

5. Riboflavin-overproducing strains of Lactobacillus fermentum for riboflavin-enriched bread.

6. Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.

7. Formation of roseoflavin from guanine through riboflavin.

8. Roseoflavin is a natural antibacterial compound that binds to FMN riboswitches and regulates gene expression.

9. Saccharomyces cerevisiae THI4p is a suicide thiamine thiazole synthase.

10. Structural and kinetic studies on RosA, the enzyme catalysing the methylation of 8-demethyl-8-amino-d-riboflavin to the antibiotic roseoflavin.

1. The hidden enzymology of bacterial natural product biosynthesis.

2. Oxidation of the FAD cofactor to the 8-formyl-derivative in human electron-transferring flavoprotein.

3. Structures and function of a tailoring oxidase in complex with a nonribosomal peptide synthetase module.

Review 4. Noncanonical Functions of Enzyme Cofactors as Building Blocks in Natural Product Biosynthesis.

5. A biosynthetic pathway to aromatic amines that uses glycyl-tRNA as nitrogen donor.