20275-13-2

Upstream product

• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 98-59-9 p-toluenesulfonyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 1076189-60-0 methyl (2S,4R)-4-((methylsulfonyl)oxy)-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 1350470-17-5 (2S,4S)-methyl 4-(4-(4-cyanophenyl)-1H-1,2,3-triazol-1-yl)-1-tosylpyrrolidine-2-carboxylate 
• 81519-89-3 methyl (2S,4S)-4-amino-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina

A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N2-β-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5- hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild, and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd.

Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors

A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds against SKOV3, HL60 and A549 cells were also investigated. Comparing with the control LY52, compound 12u, with excellent activity both in the enzymatic inhibition assay and cell-based assay, could be used as lead compound for the further development of MMP inhibitors.