| Title: | Enzymatic Cascade in Pseudomonas that Produces Pyrazine from alpha-Amino Acids |
| Author(s): | Masuo S; Tsuda Y; Namai T; Minakawa H; Shigemoto R; Takaya N; |
| Address: | "Faculty of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8572, Japan" |
| ISSN/ISBN: | 1439-7633 (Electronic) 1439-4227 (Linking) |
| Abstract: | "Pyrazines are widespread chemical compounds that include pheromones and odors. Herein, a novel mechanism used by Pseudomonas fluorescens SBW25 to biosynthesize monocyclic pyrazines is reported. Heterologous expression of the papABC genes that synthesize the natural alpha-amino acid 4-aminophenylalanine (4APhe), together with three adjacent papDEF genes of unknown function, in Escherichia coli resulted in the production of 2,5-dimethyl-3,6-bis(4-aminobenzyl)pyrazine (DMBAP), which comprised two symmetrical aminobenzyl moieties derived from 4APhe. It is found that PapD is a novel amino acid C-acetyltransferase, which decarboxylates and transfers acetyl residues to 4APhe, to generate an alpha-aminoketone, which spontaneously dehydrates and condenses to give dihydro DMBAP. PapF is a novel oxidase in the amine oxidase superfamily that oxidizes dihydro DMBAP to yield the pyrazine ring of DMBAP. These two enzymes constitute a unique mechanism for synthesizing monocyclic pyrazines and might serve as a novel strategy for the enzymatic synthesis of pyrazine derivatives from natural alpha-amino acids" |
| Keywords: | Acetyltransferases/chemistry/*metabolism Amino Acids/chemistry/*metabolism Molecular Structure Oxidoreductases/chemistry/*metabolism Pseudomonas fluorescens/*enzymology Pyrazines/chemistry/*metabolism amino acids biosynthesis nitrogen heterocycles oxidase; |
| Notes: | "MedlineMasuo, Shunsuke Tsuda, Yusuke Namai, Tomohito Minakawa, Hajime Shigemoto, Ryosuke Takaya, Naoki eng Research Support, Non-U.S. Gov't Germany 2019/07/20 Chembiochem. 2020 Feb 3; 21(3):353-359. doi: 10.1002/cbic.201900448. Epub 2019 Nov 6" |
