17791-52-5Relevant articles and documents
An improved synthesis of tert butyloxycarbonyl L histidine
Van Batenburg,Kerling
, p. 1 - 2 (1976)
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The microenvironment and pKaperturbation of aminoacyl-tRNA guided the selection of cationic amino acids
Hazra, Bibhas,Prasad, Mahesh,Roy, Rajat,Tarafdar, Pradip K.
supporting information, p. 8049 - 8056 (2021/10/04)
The proteinogenic lysine (Lys) and arginine (Arg) have multiple methylene groups between α-carbon and the terminal charged centre. Why nature did not select ornithine (Orn), 2,4-diamino butyric acid (Dab) and 2,3-diamino propionic acid (Dpr) with fewer methylene groups in the side chain remains an important question! The propensity of aminoacyl-tRNA (aa-tRNA) model substrates towards self-degradationviaintramolecular lactamization was studied using UV spectroscopy and1H-NMR titration, which showed that Lys and Arg remain stable, and Orn and Dab cyclize to lactam. Hydrophobicity-assisted surface mediated model peptide formation highlighted that the microenvironment and pKaperturbation led to poor regioselectivity (α-aminevs.terminal amine) in Dpr and other non-proteinogenic analogues. The α-selectivity became even poorer in the presence of phosphate, making them ill-suited for peptide synthesis. Superior regioselectivity of the Lys aa-tRNA model substrate suggests that the extra methylene bridge helped nature to separate the microenvironments of the α-amine and ε-amine to synthesize the peptide backbone.
Synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine
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Paragraph 0030; 0032-0033; 0035-0036; 0038-0039; 0041, (2020/09/09)
The invention relates to a synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine, which comprises the following steps of: dissolving solid L-histidine in a sodium carbonate water solution, dropwisely adding liquid di-tert-butyl dicarbonate, reacting, filtering, and washing the filtrate with an organic solvent to remove unreacted di-tert-butyl dicarbonate; after the reaction solution is subjected to aqueous phase acidification, adding an extracting agent ethyl acetate for extraction, conducting standing and layering, and washing, drying and filtering an oil phase to obtain an ethyl acetate solution containing an intermediate N alpha-tert-butyloxycarbonyl-Nim-tert-butyloxycarbonyl-L-histidine; stirring the ethyl acetate solution containing the intermediate N alpha-tert-butyloxycarbonyl-Nim-tert-butyloxycarbonyl-L-histidine at 50-100 DEG C for reaction, and after the reaction is finished, carrying out after-treatment to obtain the product N alpha-tert-butyloxycarbonyl-L-histidine.The synthesis method of N alpha-tert-butyloxycarbonyl-L-histidine provided by the invention is simple in process and convenient to operate, the product purity and yield are higher than those in the prior art, the technical problem that purification and desalination are not thorough by using ion exchange resin is solved, and the synthesis method is suitable for industrial production.
Discovery of a Membrane-Active, Ring-Modified Histidine Containing Ultrashort Amphiphilic Peptide That Exhibits Potent Inhibition of Cryptococcus neoformans
Sharma, Krishna K.,Maurya, Indresh Kumar,Khan, Shabana I.,Jacob, Melissa R.,Kumar, Vinod,Tikoo, Kulbhushan,Jain, Rahul
, p. 6607 - 6621 (2017/08/17)
The new structural classes of ultrashort peptides that exhibit potent microbicidal action have potential as future drugs. Herein, we report that C-2 arylated histidines containing tripeptides His(2-Ar)-Trp-His(2-Ar) exhibit potent antifungal activity against Cryptococcus neoformans with high selectivity. The most potent peptide 12f [His(2-biphenyl)-Trp-His(2-biphenyl)] displayed high in vitro activity against C. neoformans (IC50 = 0.35 μg/mL, MIC = MFC = 0.63 μg/mL) with a selectivity index of >28 and 2 times higher potency compared to amphotericin B. Peptide 12f exhibited proteolytic stability, with no apparent hemolytic activity. The mechanism of action study of 12f by confocal laser scanning microscopy and electron microscopy indicates nuclear fragmentation and membrane disruption of C. neoformans cells. Combinations of 12f with fluconazole and amphotericin B at subinhibitory concentration were synergistic against C. neoformans. This study suggests that 12f is a new structural class of amphiphilic peptide with rapid fungicidal activity caused by C. neoformans.
