139008-70-1

Basic information

• Product Name: L-Proline, 1-[N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl]-, methyl ester
• CAS NO: 139008-70-1
• Molecular Formula: C17H26N4O5
• Molecular Weight: 366.417
• Mol File: 139008-70-1.mol

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-[N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-[N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl]-, methyl ester(139008-70-1)
• EPA Substance Registry System: L-Proline, 1-[N-[(1,1-dimethylethoxy)carbonyl]-L-histidyl]-, methyl ester(139008-70-1)

Safety Data

• Hazardous Substances Data: 139008-70-1(Hazardous Substances Data)

Upstream product

• 2133-40-6 L-proline methyl ester monohydrochloride 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 

Downstream Products

• 1423168-04-0 cyclo-D-Pro-L-(Phe-Pro-His-Pro-Pro-Gly-Leu) 
• 1258668-78-8 Boc-Phe-Pro-His-Pro-OMe 
• 1341194-86-2 C₂₆H₃₄N₆O₅ 
• 945264-89-1 (CH₃)2C₇H₃N₂C₆H₂I₂CONHCHCH₂C₃H₃N₂CONC₄H₇CO₂CH₃ 

Relevant articles and documents

Copper-Promoted N-Arylation of the Imidazole Side Chain of Protected Histidine by Using Triarylbismuth Reagents

The N-arylation of the side chain of histidine by using triarylbismuthines is reported. The reaction is promoted by copper(II) acetate in dichloromethane at 40 °C under oxygen in the presence of diisopropylethylamine and 1,10-phenanthroline and allows the transfer of aryl groups with substituents at any position of the aromatic ring. The reaction shows excellent functional group tolerance and is applicable to dipeptides where the histidine is located at the N terminus. A histidine-guided backbone N?H arylation was observed in dipeptides where the histidine occupies the C terminus.

Five- and six-membered nitrogen-containing compounds as selective carbonic anhydrase activators

It has been proven that specific isoforms of human carbonic anhydrase (hCA) are able to fine-tune physiological pathways connected to signal processing, and that decreased CAs expression negatively influences cognition, leading to mental retardation, Alzheimer’s disease, and aging-related cognitive dysfunctions. For this reason, a small library of natural and synthetic nitrogen containing cyclic derivatives was assayed as activators of four human isoforms of carbonic anhydrase (hCA I, II, IV and VII). Most of the compounds activated hCA I, IV and VII in the micromolar range, with KAs ranging between 3.46 and 80.5 μM, whereas they were not active towards hCA II (KAs > 100 μM). Two natural compounds, namely L-(+)-ergothioneine (1) and melatonin (2), displayed KAs towards hCA VII in the nanomolar range after evaluation by a CO2 hydration method in vitro, showing a rather efficient and selective activation profile with respect to histamine, used as a reference compound. Corroborated with the above in vitro findings, a molecular modelling in silico approach has been performed to correlate these biological data, and to elucidate the binding interaction of these activators within the enzyme active site.

Synthesis, docking and anticancer activity studies of D-proline- incorporated wainunuamide

D-proline-incorporated wainunuamide - a cyclic octapeptide was synthesized and characterized by FTIR, 1H and 13C NMR and Mass spectral analysis. Molecular docking studies were carried out for the designed cyclic octapeptide and the results showed greater affinity for HPV18-2IOI receptor (HeLa cancer cell line). The synthesized cyclic octapeptide exhibited potent anticancer activity against HeLa cancer cells. Indian Academy of Sciences.

Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential

Four substituted benzimidazolyl-benzoic/salicylic acids 5-8 were synthesized by interaction of 5,6-dimethyl-/6-nitrobenzimidazoles with diazotized substituted/unsubstituted aminobenzoic acids in the presence of cupric chloride. The coupling of compounds 5-8 with different amino acid ester hydrochlorides/dipeptide/tripeptide/tetrapeptide methyl esters afforded novel benzimidazolopeptide derivatives 5a-f, 6a-h, 7a-g and 8a-g. The structures of all newly synthesized compounds were established on the basis of analytical, IR, 1H NMR, 13C NMR and mass spectral data. Selected peptide ester derivatives were further hydrolyzed by using lithium hydroxide (LiOH) to yield corresponding acid derivatives 5ba-da, 6ea-ga, 7ca-ea and 8ea-ga. All peptide derivatives were screened for their antimicrobial, anthelmintic and cytotoxic activities. Almost all newly synthesized benzimidazolopeptides have shown moderate to good anthelmintic activity against all three earthworm species and good antimicrobial activity against pathogenic fungal strains Candida albicans and Aspergillus niger, gram negative bacterial strains Pseudomonas aeruginosa and Escherichia coli. Compounds 8g and 8ga possessed significant cytotoxic activity against Dalton's lymphoma ascites (DLA) and Ehrlich's ascites carcinoma (EAC) cell lines.