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.
Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores
Zwick, Christian R.,Sosa, Max B.,Renata, Hans
supporting information, p. 1673 - 1679 (2021/01/25)
The GE81112 complex has garnered much interest due to its broad antimicrobial properties and unique ability to inhibit bacterial translation initiation. Herein we report the use of a chemoenzymatic strategy to complete the first total synthesis of GE81112 B1. By pairing iron and α-ketoglutarate dependent hydroxylases found in GE81112 biosynthesis with traditional synthetic methodology, we were able to access the natural product in 11 steps (longest linear sequence). Following this strategy, 10 GE81112 B1 analogues were synthesized, allowing for identification of its key pharmacophores. A key feature of our medicinal chemistry effort is the incorporation of additional biocatalytic hydroxylations in modular analogue synthesis to rapidly enable exploration of relevant chemical space.
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.