72156-59-3

Basic information

• Product Name: methyl N-(tert-butoxycarbonyl)tryptophylhistidinate
• CAS NO: 72156-59-3
• Molecular Formula: C₂₃H₂₉N₅O₅
• Molecular Weight: 455.5069
• Mol File: 72156-59-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 783.5°C at 760 mmHg
• Flash Point: 427.6°C
• Density: 1.284g/cm³
• Vapor Pressure: 1.68E-24mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: methyl N-(tert-butoxycarbonyl)tryptophylhistidinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(tert-butoxycarbonyl)tryptophylhistidinate(72156-59-3)
• EPA Substance Registry System: methyl N-(tert-butoxycarbonyl)tryptophylhistidinate(72156-59-3)

Safety Data

• Hazardous Substances Data: 72156-59-3(Hazardous Substances Data)

Upstream product

• 13139-14-5 Boc-Trp-OH 
• 1604-44-0 N-α-trifluoroacetyl-L-histidine methyl ester 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 
• 71-00-1 L-histidine 
• 71-00-1 L-histidine 
• 1604-44-0 N-α-trifluoroacetyl-L-histidine methyl ester 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 1499-46-3 L-Histidine methyl ester 
• 4467-54-3 histidine methyl ester hydrochloride 

Downstream Products

• 1415241-39-2 Boc-His-Trp-His-OMe 
• 1610930-66-9 His-Trp-His-OMe 

Relevant articles and documents

Discovery of a Membrane-Active, Ring-Modified Histidine Containing Ultrashort Amphiphilic Peptide That Exhibits Potent Inhibition of Cryptococcus neoformans

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.

Synthetically modified l-histidine-rich peptidomimetics exhibit potent activity against Cryptococcus neoformans

We describe the synthesis and antimicrobial evaluation of structurally new peptidomimetics, rich in synthetically modified l-histidine. Two series of tripeptidomimetics were synthesized by varying lipophilicity at the C-2 position of l-histidine and at the N- and C-terminus. The data indicates that peptides (5f, 6f, 9f and 10f) possessing highly lipophilic adamantan-1-yl group displayed strong inhibition of Cryptococcus neoformans. Peptide 6f is the most potent of all with IC50 and MFC values of 0.60 and 0.63 μg/mL, respectively, compared to the commercial drug amphotericin B (IC50 = 0.69 and MFC = 1.25 μg/mL). The selectivity of these peptides to microbial pathogen was examined by a tryptophan fluorescence quenching study and transmission electron microscopy. These studies indicate that the peptides plausibly interact with the mimic membrane of pathogen by direct insertion, and results in disruption of membrane of pathogen.

Solvent-free peptide synthesis assisted by microwave irradiation: Environmentally benign synthesis of bioactive peptides

An efficient and facile, solvent-free peptide synthesis assisted by microwave irradiation, using DIC/HONB as the coupling reagent combination is reported. Key features of this original protocol are solvent-free synthesis, very short reaction time and scal