344-25-2Relevant articles and documents
Irreversible inhibitors of the proline racemase unveil innovative mechanism of action as antibacterial agents against Clostridioides difficile
Barbut, Frédéric,Blondel, Arnaud,Gateau, Cécile,Gouault, Nicolas,Melo, Guilherme D.,Minoprio, Paola,Renault, Jacques,Tasseau, Olivier,Uriac, Philippe
, (2022/01/11)
Proline racemases (PRAC), catalyzing the l-proline and d-proline interconversion, are essential factors in eukaryotic pathogens such as Trypanosoma cruzi, Trypanosoma vivax, and Clostridioides difficile. If the discovery of irreversible inhibitors of T.?cruzi PRAC (TcPRAC) led to innovative therapy of the Chagas disease, no inhibitors of CdPRAC have been discovered to date. However, C.?difficile, due to an increased incidence in recent years, is considered as a major cause of health threat. In this work, we have taken into account the similarity between TcPRAC and CdPRAC enzymes to design new inhibitors of CdPRAC. Starting from (E) 4-oxopent-2-enoic acid TcPRAC irreversible inhibitors, we synthesized 4-aryl substituted analogs and evaluated their CdPRAC enzymatic inhibition against eleven strains of C.?difficile. This study resulted in promising candidates and allowed for identification of (E)-4-(3-bromothiophen-2-yl)-4-oxobut-2-enoic acid 20 that was chosen for complementary in vivo studies and did not reveal in vivo toxicity.
Cyclic tetrapeptides from the marine strain Streptomyces sp. PNM-161a with activity against rice and yam phytopathogens
Betancur, Luz A.,Forero, Abel M.,Romero-Otero, Adriana,Sepúlveda, Lady Yohanna,Moreno-Sarmiento, Nubia C.,Castellanos, Leonardo,Ramos, Freddy A.
, p. 744 - 751 (2019/07/05)
Two cyclotetrapeptides, henceforth named Provipeptides A (1) and B (2), along with five known diketopiperazines (3–7) were isolated from the liquid culture of marine Streptomyces sp. 161a recovered from a sample of sea grass Bryopsis sp. The structures of cyclotetrapeptides and diketopiperazines (DKPs) were established by 1D and 2D NMR data, MS, and by comparison with literature data. The absolute stereochemistry of compounds cyclo-(l-Pro-l-Leu-d-Pro-l-Phe) 1 and cyclo-(-Pro-Ile-Pro-Phe) 2 was established by the Marfey’s method. Compound 1 showed antibacterial activity against rice phytopathogenic strains Burkholderia glumae (MIC = 1.1 mM) and Burkholderia gladioli (MIC = 0.068 mM), compound 2 was active only against B. glumae (MIC = 1.1 mM), and DKP cyclo-[l-Pro-l-Leu] 5 showed to be active against B. gladioli (MIC = 0.3 mM) and B. glumae (MIC = 2.4 mM). Compounds 1 and 2 showed 65% and 50% inhibition of Colletotrichum gloeosporioides (yam pathogen) conidia germination, respectively at a concentration of 1.1 mM.
Method for synthesizing D-proline
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Paragraph 0026; 0030-0032; 0035, (2018/07/30)
The invention belongs to the technical field of synthesis of chiral organic compounds, and especially relates to a method for synthesizing D-proline. The method comprises the following steps: taking pyrrolidine-2-carbaldehyde, dissolving the pyrrolidine-2-carbaldehyde in an organic solvent, adding a catalyst and an organic alkali potassium t-butoxide, and carrying out an asymmetric catalysis hydrogenation reaction to obtain an intermediate II; and carrying out an oxidation reaction on the intermediate II and an oxidant to obtain the product D-proline III. The method for synthesizing D-prolinehas the following advantages: the use amount of the catalyst is small, and the catalyst can be used repeatedly, so the cost is saved; the solvent used in the synthesis process is a common solvent, sothe method has the characteristics of low cost, non-toxicity, no pollution, greenness and environmental protection; and the synthesis method has a simple process, the yield in the invention is higherthan the yield in the prior art, and the optical purity of the obtained product is high, so the method is suitable for industrial production.
