128425-02-5

Basic information

• Product Name: L-Proline, 1-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-
• CAS NO: 128425-02-5
• Molecular Formula: C14H17N5O7
• Molecular Weight: 367.318
• Mol File: 128425-02-5.mol
• Article Data: 54

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128425-02-5)
• EPA Substance Registry System: L-Proline, 1-[5-[(2-amino-1-methyl-2-oxoethyl)amino]-2,4-dinitrophenyl]-, (S)-(128425-02-5)

Safety Data

• Hazardous Substances Data: 128425-02-5(Hazardous Substances Data)

Upstream product

• 1037224-61-5 mollamide B 
• 95713-52-3 N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide 
• 1037224-63-7 mollamide C 
• 1312794-02-7 minutissamide A 
• 1312415-68-1 brachystemin I 
• 1312415-67-0 brachystemin H 
• 1312415-66-9 brachystemin G 
• 1312415-65-8 brachystemin F 
• 1236074-96-6 trichoderin B 
• 1236074-95-5 trichoderin A₁ 
• 1236074-94-4 trichoderin A 
• 1191116-28-5 alternaramide 
• 147-85-3 L-proline 
• 609-36-9 rac-Pro-OH 

Relevant articles and documents

Genomics-driven discovery of a new cyclodepsipeptide from the guanophilic fungusAmphichorda guana

Two potential non-ribosomal peptide synthetases (NRPSs) were identified in the genome of a guanophilic fungusAmphichorda guanaby bioinformatics analysis and gene knockout experiments. Liquid chromatography coupled with mass spectrometry (LC-MS) guided isolation led to the discovery of a new cyclodepsipeptide isaridin H (1) and seven known analogs, desmethylisaridin E (2), isaridin E (3), isariin A (4), iso-isariin B (5), iso-isariin D (6), isariin E (7), and nodupetide (8). The absolute configuration of isaridin H (1) was achieved by Marfey's method. Isaridin H (1) showed significant antifungal activity againstBotrytis cinereaandAlternaria solani.

An inhibitor of CCL2-induced chemotaxis from the fungus Leptoxyphium sp.

A biological screen used to identify inhibitors of monocyte chemotactic protein-1 (CCL2)-induced chemotaxis was applied in the activity-guided fractionation of an extract from a fungus of the genus Leptoxyphium sp. Inhibition of CCL2-induced chemotaxis was traced to a new dichlorinated diketopiperazine, cyclo(13,15-dichloro-L-Pro-L-Tyr). A structure-activity relationship (SAR) study evaluating relative activities of cyclo(13,15-dichloro- L-Pro-L-Tyr) and a nonchlorinated homologue cyclo(L-Pro-L-Tyr) showed that the dichlorinated molecule was 10- to 20-fold more active than the nonchlorinated form, while no activity was observed for cyclo(D-N-methylLeu-L-Trp).

Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4

Three new cyclopentapeptides, versicoloritides A-C (1-3), a new orcinol tetramer, tetraorcinol A (4), and two new lactones, versicolactones A and B (5 and 6) together with three known metabolites, diorcinol, glyantrypine, and cordyol C were isolated from the fermentation broth of the coral-associated fungus Aspergillus versicolor LCJ-5-4. Their structures were elucidated by spectroscopic and chemical methods. The new compounds 1-4 were evaluated for their radical-scavenging activity and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans and cytotoxicity against P388 and Hela cell lines. Compound 4 showed weak radical-scavenging activity against the DPPH radical with an IC50 value of 67 μM.

Isolation and assessment of the in vitro anti-tumor activity of smenothiazole a and B, chlorinated thiazole-containing peptide/polyketides from the Caribbean sponge, Smenospongia aurea

The study of the secondary metabolites contained in the organic extract of Caribbean sponge Smenospongia aurea led to the isolation of smenothiazole A ( 3) and B (4), hybrid peptide/polyketide compounds. Assays performed using four solid tumor cell lines

A new analogue of echinomycin and a new cyclic dipeptide from a marine-derived streptomyces sp. LS298

Quinomycin G (1), a new analogue of echinomycin, together with a new cyclic dipeptide, cyclo-(L-Pro-4-OH-L-Leu) (2), as well as three known antibiotic compounds tirandamycin A (3), tirandamycin B (4) and staurosporine (5), were isolated from Streptomyces

Lyngbyacyclamides A and B, novel cytotoxic peptides from marine cyanobacteria Lyngbya sp.

Lyngbyacyclamides A (1) and B (2), novel cyclic peptides, were isolated from marine cyanobacteria Lyngbya sp. collected in Okinawa, Japan. Their structures were determined by spectroscopic analyses and degradation studies. They moderately inhibited the growth of B16 mouse melanoma cells.

Asperaculanes a and b, two sesquiterpenoids from the fungus Aspergillus aculeatus

Six sesquiterpenoids 1-6, including two new ones, an ent -daucane-type sesquiterpenoid, asperaculane A (1), and a nordaucane one, asperaculane B (2), and four known nordaucane derivatives, aculenes A-D 3-6, together with the known secalonic acid D (7), were isolated from a fermentation culture of the fungus Aspergillus aculeatus. Their structures and absolute configurations were established by analyses of their spectroscopic data, including 1D and 2D-NMR spectra, HR-ESIMS, electronic circular dichroism (ECD) data, and quantum chemical calculations. These metabolites were evaluated for in vitro cytotoxic activity against two cell lines, human cancer cell lines (HeLa) and one normal hamster cell line (CHO).

Acaricidal Activity of Cyclodipeptides from Bacillus amyloliquefaciens W1 against Tetranychus urticae

Bioassay-guided fractionation of the supernatant of the biocontrol strain Bacillus amyloliquefaciens W1 led to the isolation of eight acaricidal cyclodipeptides from the active fractions by column chromatography separation and HPLC purification. The chemi

Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria

Two bioactive cyclic dipeptides, cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr), were isolated from the culture broth of Streptomyces sp. strain 22-4 and tested against three economically important plant pathogens, Xanthomonas axonopodis pv. citri, Ralstonia s

Cyclic heptapeptides, cordyheptapeptides C-E, from the marine-derived fungus Acremonium persicinum SCSIO 115 and their cytotoxic activities

Three new cycloheptapeptides, cordyheptapeptides C-E (1-3), were isolated from the fermentation extract of the marine-derived fungus Acremonium persicinum SCSIO 115. Their planar structures were elucidated on the basis of extensive MS, as well as 1D and 2

Stylissamide I, a new cyclic heptapeptide from an okinawan marine sponge Stylissa sp.

A new cyclic heptapeptide, stylissamide I (1), was isolated from an Okinawan marine sponge Stylissa sp. The structure of stylissamide I (1) was elucidated to be cyclo-(L-Tyr1-L-Tyr2-L-Tyr3-L-Pro1-L-Pro2-L-Val-L-Pro3) by extensive spectral analyses and Marfey's method. Stylissamide I (1) showed antifungal activity against Aspergillus Niger.

Leveraging Peptaibol Biosynthetic Promiscuity for Next-Generation Antiplasmodial Therapeutics

Malaria remains a worldwide threat, afflicting over 200 million people each year. The emergence of drug resistance against existing therapeutics threatens to destabilize global efforts aimed at controlling Plasmodium spp. parasites, which is expected to leave vast portions of humanity unprotected against the disease. To address this need, systematic testing of a fungal natural product extract library assembled through the University of Oklahoma Citizen Science Soil Collection Program has generated an initial set of bioactive extracts that exhibit potent antiplasmodial activity (EC50 25 μM, selectivity index > 250). The unique chemodiversity afforded by these fungal isolates serves to unlock new opportunities for translating peptaibols into a bioactive scaffold worthy of further development.

Ectyoplasin, a novel cytotoxic cyclic peptide from Ectyoplasia ferox sponge

A new cyclic heptapeptide, ectyoplasin (1), was isolated from a methanol extract of the sponge Ectyoplasia ferox. The planar structure of 1, cyclo(-Leu1-Asn2-Ala3-Val4-Thr5-Pro6-Gly7-), was determined by one and two-dimensional NMR spectroscopy and high-resolution tandem mass spectrometry. Its absolute stereochemistry was solved by Marfey’s method. The in vitro assays show that ectyoplasin (1) possess significant cytotoxic activity (2.9 ? 23.5 μM) against the cell lines, DU-145 (human prostate cancer), Jurkat (human T-cell acute leukaemia), MM144 (human multiple myeloma), HeLa (human cervical carcinoma) and CADO-ES1 (human Ewing’s sarcoma). The DU-145 cell line showed apoptotic cell death in response to ectyoplasin (1) treatment.