4298-08-2Relevant articles and documents
Microbial screening in hydroxylation of l-proline
Bontoux,Gelo-Pujic
, p. 9073 - 9076 (2006)
Microbial screening of 250 wild type strains resulted in identification of five strains with the activity of prolyl hydroxylase. All five strains hydroxylated regioselectively and enantioselectively l-proline into 4(R)-trans-hydroxy-l-proline 1. The best conversions were obtained with a wild type of Aeromonas caviae. 3-Hydroxylase activity was not detected.
Total Synthesis of 3(S)-Carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine, an Unusual Amino Acid Constituent of Luzopeptin A
Hughes, Philip,Clardy, Jon
, p. 3260 - 3264 (1989)
The enantiospecific synthesis of 3(S)-carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine (2), a novel constituent of the antibiotic antitumor agent luzopeptin A is described.Structural corroboration of the synthetic compound is based on three points.The 13C NMR spectrum of synthetic 2 was compared with that of a similar degradation product of luzopeptin.The 1H NMR spectrum of 2 was compared with that of the synthetic cis isomer.Finally, the synthetic methodology developed for the synthesis of 2 was applied to the synthesis of the known L-trans-3-hydroxyproline.
Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline
Dussauge, Solene,Moore, Charles,Snajdrova, Radka,Tassano, Erika,Vargas, Alexandra
supporting information, (2022/02/09)
Genome mining for novel Fe(II)/α-ketoglutarate-dependent dioxygenases (αKGDs) to expand the enzymatic repertoire in the oxidation of l-proline is reported. Through clustering of proteins, we predicted regio- and stereoselectivity in the hydroxylation reaction and validated this hypothesis experimentally. Two novel byproducts in the reactions with enzymes from Bacillus cereus and Streptomyces sp. were isolated, and the structures were determined to be a 3,4-epoxide and a 3,4-diol, respectively. The mechanism for the formation of the epoxide was investigated by performing an 18O-labeling experiment. We propose that the mechanism proceeds via initial cis-3-hydroxylation followed by ring closure. A biocatalytic step was run on subgram quantities of starting material without any significant optimization of the conditions. However, the substrate concentration was 40-fold higher than the usual reported titers for recombinant P450-mediated hydroxylations, showing the synthetic potential of αKGDs on a preparative scale.
Preparation method of cis-3-hydroxyl-L-proline
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Paragraph 0014; 0038; 0046; 0047; 0055, (2019/02/04)
The invention provides a preparation method of cis-3-hydroxyl-L-proline. The preparation method comprises the following steps of using the industrially produced L-serine as the starting raw material,introducing a second chiral center into the nucleophilic addition reaction of aldehyde via an ortho chiral induction format, and separating the product and an isomer by a column separating method; constructing an intermediate of which the carbon number is the same with the carbon number of a target product through the hydroxyl protection and the hydroboration-oxidizing reaction, constructing a five-elemental ring of the proline via the cyclization reaction in molecules, and removing the protective radicals, so as to obtain the cis-3-hydroxyl-L-proline. The cis-3-hydroxyl-L-proline prepared bythe preparation method has the advantages that the chemical purity and optical purity are high; the whole technology is simple and is easy to implement, the cost is low, the expensive or hypertoxic raw material or reagent is not used, and the cis-3-hydroxyl-L-proline is suitable for kilogram-level production; the higher implementing value and social and economic benefits are realized.