title: Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases.
abstract: We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to l-proline and l-pipecolinic acid, we found that 3,4-dehydro-l-proline, l-azetidine-2-carboxylic acid, cis-3-hydroxy-l-proline, and l-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-l-proline, cis-3-hydroxy-l-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-l-proline.
authors.affiliation: a Research Institute for Science and Engineering , Waseda University , Tokyo , Japan.
authors.forename: Ryotaro
authors.initials: R
authors.lastname: Hara
authors.forename: Naoko
authors.initials: N
authors.lastname: Uchiumi
authors.forename: Naoko
authors.initials: N
authors.lastname: Okamoto
authors.forename: Kuniki
authors.initials: K
authors.lastname: Kino
mesh_terms: D001419:Bacteria / Q000201:enzymology*; D049308:Dioxygenases / Q000378:metabolism*; D007656:Ketoglutaric Acids / Q000378:metabolism*; D010100:Oxygen / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007656:Ketoglutaric Acids; D011392:Proline; D049308:Dioxygenases; D010100:Oxygen
keywords: dihydroxyproline; dioxygenase; hydroxylase; oxygenation; proline derivative