Biosynthesis of 4-Methylproline in Cyanobacteria: Cloning of nosE and nosF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities
- 28 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (1) , 83-91
- https://doi.org/10.1021/jo026479q
Abstract
The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.Keywords
This publication has 17 references indexed in Scilit:
- Studies on the Biosynthesis of Paraherquamide: Concerning the Mechanism of the Oxidative Cyclization of l-Isoleucine to β-MethylprolineJournal of the American Chemical Society, 2001
- Isolation and Structure Determination of Nostocyclopeptides A1 and A2 from the Terrestrial Cyanobacterium Nostoc sp. ATCC53789Journal of Natural Products, 2000
- Herstellung von ‘Semialdehyd’‐Derivaten von Asparaginsäure‐ und Glutaminsäure durch Rosenmund‐ReduktionHelvetica Chimica Acta, 1990
- Chirospecific synthesis of .beta.-hydroxy .alpha.-amino acidsThe Journal of Organic Chemistry, 1989
- The stereospecificity of the ferrous‐ion‐dependent alcohol dehydrogenase from Zymomonas mobilisEuropean Journal of Biochemistry, 1989
- Scytonemin A, a novel calcium antagonist from a blue-green algaThe Journal of Organic Chemistry, 1988
- Vibrational circular dichroism of polypeptides. 8. Poly(lysine) conformations as a function of pH in aqueous solutionJournal of the American Chemical Society, 1986
- Reactions of resonance stabilized anions. 35. Electron transfer processes. 18. Reaction of 2-halo-2-nitropropanes and 2,2-dinitropropane with resonance-stabilized carbanions and 1-alkynyllithiumsJournal of the American Chemical Society, 1979
- A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye bindingAnalytical Biochemistry, 1976
- A NMR investigation of proline and its derivatives. II—Conformational implications of the 1H NMR spectrum of L‐proline at different pHMagnetic Resonance in Chemistry, 1975