83825-04-1Relevant articles and documents
Synthesis, characterization and antimicrobial activity of protected dipeptides and their deprotected analogs
Gill, Jatinder Pal Kaur,Singh, Simranjeet,Sethi, Nidhi
, p. 417 - 421 (2015/06/30)
Peptides are the chemical compounds which consist of amino acids coupled together by peptide linkage. Peptide derivatives are synthesized by coupling the carboxyl group of one amino acid with amino group of other. Due to the possibilities of fortuitous and unintentional reactions, various protecting groups are used to protect the carboxylic acid as well as amino groups of both the amino acids. These peptide derivatives are associated with a variety of pharmacological activities including antibacterial and antifungal activities. While doing our analysis some of the dipeptides were synthesized in a reasonable yield and purity which were fully characterised by FTIR and H1 NMR. The antimicrobial activity of these derivatives was studied and these were found to be active against two strains of fungi (Aspergillus fumigatus & Pencillium chrysogenum) and two strains of bacteria (E. coli and Salmonella typhimurium). This provides for a future insight to work on the synthesis of these dipeptide derivatives to achieve their stability.
Concise diastereoselective synthesis of calcaripeptide C via asymmetric transfer hydrogenation/Pd-induced chiral allenylzinc as a key reaction
Kumaraswamy, Gullapalli,Narayanarao, Vykunthapu,Raju, Ragam
supporting information, p. 8487 - 8494 (2015/08/06)
Synthesis of the natural product calcaripeptide C derived from the fungal metabolite mycelium KF525 of Calcarisporium sp. has been achieved. This complementary approach avoids the use of a stoichiometric amount of chiral auxiliary reagents as commonly used to generate enantioenriched advanced precursors. The enantioselective synthesis of calcaripeptide C is remarkable in that using catalytic reactions sets the two stereogenic centers efficiently with good levels of enantioselectivity. Further diversification of the calcaripeptide C structures is possible by employing a complementary catalytic enantioenriched Ru-catalyst.
Stereoselective total synthesis of marine cyclodepsipeptide calcaripeptides A-C
Das, Sayantan,Kumar Goswami, Rajib
, p. 9778 - 9791 (2015/02/19)
The first stereoselective total syntheses of marine cyclodepsipeptides, calcaripeptides A-C, have been accomplished. Emphasis was given particularly in identification of an efficient strategy for the macrocyclization. The notable features of our synthesis include Evans alkylation, Crimmins syn-aldol, Crimmins acetate aldol, Wittig olefination, and Shiina macrolactonization reactions. An anomaly in the 1H NMR of the proposed calcaripeptide B has been amended during this synthetic study. (Chemical Equation Presented).
Discovery of dipeptide-derived catalysts for the enantioselective addition of dimethylzinc to aldehydes
Kang, Seock Yong,Park, Yong Sun
supporting information; experimental part, p. 1703 - 1706 (2012/05/04)
A new class of modular chiral catalysts derived from various amino acid-L-Pro dipeptides was prepared, and the catalysts were tested for their ability to catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes. Dipeptides derived from L-Asp-L-Pro were identified as effective catalysts for the addition at room temperature with up to 97:3er and 95% yield.
Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine-copper(II) complex
Selvakumar, Sermadurai,Sivasankaran, Dhanasekaran,Singh, Vinod K.
supporting information; experimental part, p. 3156 - 3162 (2011/02/25)
A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral aziridine in few steps.
Synthesis and pharmacological investigation of segetalin C as a novel antifungal and cytotoxic agent
Dahiya, Rajiv,Kaur, Komalpreet
, p. 29 - 34 (2008/09/19)
In present study, a natural phenylalanine-rich cycloheptapeptide segetalin C (compound VIII) was synthesized by coupling and cyclization of peptide units Boc-gly-L-leu-L-his-OH and L-Phe-L-ala-L-phe-L-pro-OMe and examined for different bioactivities. The
Synthesis and biological activity of peptide derivatives of iodoquinazolinones/nitroimidazoles
Dahiya, Rajiv,Kumar, Anil,Yadav, Rakesh
, p. 958 - 976 (2008/09/20)
Two substituted quinazolinyl/imidazolyl-salicylic acids 5, 6 were synthesized by the reaction of 6-iodo-2-methylbenzoxazin-4-one/5-nitroimidazole with 5-aminosalicylic acid (5-ASA). Coupling of compounds 5 and 6 with different amino acid ester hydrochlorides, dipeptide and tripeptide methyl esters yielded novel quinazolino/imidazolopeptide derivatives 5a-f and 6a-g. The chemical structures of all newly synthesized compounds were confirmed by means of FT-IR, 1H- and 13C-NMR, MS and elemental analysis. Selected peptide ester derivatives were further hydrolyzed by using lithium hydroxide (LiOH) to afford the corresponding acid derivatives 5ba-da and 6ea-ga. All peptide derivatives were assayed for antimicrobial and anthelmintic activities against eight pathogenic microbes and three earthworm species. Among the tested compounds, 5e, 5d, 6e and their hydrolyzed analogs 5da and 6ea exhibited higher antimicrobial activity against Pseudomonas aeruginosa, Klebsiella pneumoniae and Candida albicans, and 5a, 6g and 6ga displayed better antifungal activity against the dermatophytes Trichophyton mentagrophytes and Microsporum audouinii. Moreover, 6f and its hydrolyzed derivative 6fa showed good anthelmintic activity against Megascoplex konkanensis, Pontoscotex corethruses and Eudrilus eugeniea at dose of 2 mg mL-1.
Design, synthesis, and biological evaluation of a new class of small molecule peptide mimetics targeting the melanocortin receptors
Cain, James P.,Mayorov, Alexander V.,Cai, Minying,Wang, Hui,Tan, Bahar,Chandler, Kevin,Lee, YeonSun,Petrov, Ravil R.,Trivedi, Dev,Hruby, Victor J.
, p. 5462 - 5467 (2007/10/03)
A new bicyclic template has been developed for the synthesis of peptide mimetics. Straightforward synthetic steps, starting from amino acids, allow the facile construction of a wide range of analogs. This system was designed to target the melanocortin receptors (MCRs), with functional group selection based on a known pharmacophore and guidance from molecular modeling to rationally identify positional and stereochemical isomers likely to be active. The functions of hMCRs are critical to myriad biological activities, including pigmentation, steroidogenesis, energy homeostasis, erectile activity, and inflammation. These G-protein-coupled receptors (GPCRs) are targets for drug discovery in a number of areas, including cancer, pain, and obesity therapeutics. All compounds from this series tested to date are antagonists which bind with high affinity. Importantly, many are highly selective for a particular MCR subtype, including some of the first completely hMC5R-selective antagonists reported.
Total synthesis of cis,cis-ceratospongamide, a bioactive thiazole-containing cyclic peptide from marine origin
Yokokawa,Sameshima,Shioiri
, p. 986 - 988 (2007/10/03)
The first total synthesis of cis,cis-ceratospongamide (1a), isolated from marine source, was accomplished via thiazole synthesis using CMD methodology, DEPC-mediated peptide coupling, macrolactamization, and cyclodehydration. Comparison of the cyclization sites and coupling reagents in the macrolactamization step was also investigated.
Synthesis and pharmacological study of some enkephalin analogs in relation to the plurality of opiate receptors
Audigier,Mazarguil,Gout,Cros
, p. 173 - 177 (2007/10/02)
We have synthesized a series of enkephalin analogs and measured their affinity for each type of 'opiate' receptor, the μ receptor and the δ receptor. Furthermore, we have determined their respective antinociceptive activity after intracerebroventricular i
