20898-43-5

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4467-54-3 histidine methyl ester hydrochloride 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 1499-46-3 L-Histidine methyl ester 
• 71-00-1 L-histidine 

Downstream Products

• 83468-80-8 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine methyl ester hydrochloride 
• 109013-56-1 N-(tert-butoxycarbonyl)-3-(phenylmethyl)-L-histidine, methyl ester 
• 945387-60-0 N(?)-4-methylbenzyl-N(α)-tert-butoxy-carbonyl-L-histidine methyl ester 
• 945387-59-7 N(?)-4-chlorobenzyl-N(α)-tert-butoxy-carbonyl-L-histidine methyl ester 
• 429665-92-9 2(S)-tert-butoxycarbonylamino-3-[3-(3,5-dichloro-benzyl)-3H-imidazol-4-yl]-propionic acid methyl ester 
• 111102-64-8 N-(t-Butoxycarbonyl)-3-(2-methoxybenzyl)-L-histidine methyl ester 
• 114787-92-7 3-(3-methyl-4-methoxyphenyl)methyl-N-BOC-histidine methyl ester 
• 109013-61-8 3-(phenylmethyl)-L-histidine, dihydrochloride 
• 111102-72-8 3-(2-Methoxybenzyl)-L-histidine dihydrochloride 
• 111102-71-7 3-(3-Methoxybenzyl)-L-histidine dihydrochloride 
• 111102-70-6 3-(4-Hydroxybenzyl)-L-histidine dihydrobromide 
• 111102-73-9 3-(2-Phenylethyl)-L-histidine dihydrochloride 
• 111102-68-2 3-(4-Nitrobenzyl)-L-histidine dihydrochloride 
• 111102-69-3 3-(4-Methoxybenzyl)-L-histidine dihydrochloride 

Relevant academic research and scientific papers

Development of targeted nanoparticles loaded with antiviral drugs for SARS-CoV-2 inhibition

Recently, a novel coronavirus, known as severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), has raised global concerns, being the etiological agent of the current pandemic infectious coronavirus disease 2019 (COVID-19). Specific prophylactic treatments like vaccines, have been authorized for use by regulatory bodies in multiple countries, however there is an urgent need to identify new, safe, and targeted therapeutics as post-exposure therapy for COVID-19. Among a plethora of potential pharmacological targets, the angiotensin-converting enzyme 2 (ACE2) membrane receptor, which plays a crucial role in viral entry, is representing an attractive intervention opportunity for SARS-CoV-2 antiviral discovery process. In this scenario, we envisioned that binding to ACE2 by multivalent attachment of ligands to nanocarriers incorporating antiviral therapeutics, it would increase receptor avidity and impart specificity to these nanovectors for host cells, particularly in the pulmonary tract, which is the primary entry route for SARS-CoV-2. Herein, we report the design and development of novel polymeric nanoparticles (NP), densely grafted with various ligands to selectively bind to ACE2, as innovative nanovectors for targeted drug delivery. We first evaluated the impact of these biocompatible targeted NP (TNP) on ligand binding toward ACE2 and measured their competition ability vs a model of spike protein (Lipo-S1). Next, we tested the effectiveness of the most performing nanoprotopype, TNP-1, loaded with a model anti-SARS-CoV-2 drug such as remdesivir (RDV), on antiviral activity against SARS-CoV-2 infected Vero E6 cells. The RDV-TNP-1 exhibited a significantly improved antiviral effect compared to RDV at the same concentration. Interestingly, unloaded TNP (TNP-1E) also exhibited a basal antiviral activity, potentially due to a direct competitive mechanism with viral particles for the ACE2 binding site. We also measured the anti-exopeptidase activity of TNP-1E against ACE2 protein. Collectively, these insights warrant in-depth preclinical development for our nanoprototypes, for example as potential inhalable drug carriers, with the perspective of a clinical translation.

Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine

Amino acid derivatives with a central cationic heterocyclic core (e.g., imidazolium) are biologically relevant cross-linkers of proteins and advanced glycation end (AGE) products. Here, imidazolium-containing cross-linkers were synthesized from imidazole or histidine by N-alkylation employing aspartate- and glutamate-derived mesylates as key step. Biological investigations were carried out to probe the biocompatibility of these compounds.

N(?)-2-Naphthylmethoxymethyl-Protected Histidines: Scalable, Racemization-Free Building Blocks for Peptide Synthesis

Histidine (His) racemizes with relative ease during peptide synthesis. One strategy to suppress this racemization is to protect the nitrogen atom of the imidazole moiety in His with a suitable protecting group. Among the numerous protecting groups that have already been tested, the p-methoxybenzyloxymethyl (PMBOM) group on the ?-nitrogen atom effectively suppresses the racemization. However, a large-scale synthesis of N(?)-PMBOM-protected derivatives has hitherto been hampered by the requirement of a freshly prepared unstable reagent. Herein we report the synthesis of N(?)-2-naphthylmethoxymethyl (NAPOM)-protected His derivatives, which can be prepared on a gram scale and do not suffer from the aforementioned instability problems. Furthermore, these NAPOM-protected His derivatives suppress the racemization in Boc- A nd Fmoc-based peptide synthesis.

Intracellular Reactions Promoted by Bis(histidine) Miniproteins Stapled Using Palladium(II) Complexes

The generation of catalytically active metalloproteins inside living mammalian cells is a major research challenge at the interface between catalysis and cell biology. Herein we demonstrate that basic domains of bZIP transcription factors, mutated to include two histidine residues at i and i+4 positions, react with palladium(II) sources to generate catalytically active, stapled pallado-miniproteins. The resulting constrained peptides are efficiently internalized into living mammalian cells, where they perform palladium-promoted depropargylation reactions without cellular fixation. Control experiments confirm the requirement of the peptide scaffolding and the palladium staple for attaining the intracellular reactivity.

Peptide mimetic ligands of polo-like kinase 1 polo box domain and methods of use

Novel compounds are provided that bind to polo-like kinases through the polo-box domain. In certain embodiments, the novel compounds are PEGylated peptides. The PEGylated peptides in accordance with the invention demonstrate high PBD-binding affinity. In certain embodiments, the PEGylated peptides have also achieved activities in whole cell systems. The invention also provides compounds that bind polo-like kinases through the polo-box domain and possess reduced anionic charge. Further provided are methods of design and/or synthesis of the PEGylated peptides and methods of use thereof. The invention provides methods of use of the compounds and methods of synthesis of the compounds.

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.

Total Synthesis and Functional Characterization of Selenoneine

The N-α-trimethyl 2-selenohistidine selenoneine is the selenium isolog of the natural antioxidant ergothioneine. Sulfur-to-selenium substitutions are known to endow proteins and nucleic acids with special activities. In contrast, secondary metabolites tha

Preparation method of N (tau)-methyl-L-histidine derivative and application of derivative in synthesis of anserine

The invention provides a preparation method of an N (tau)-methyl-L-histidine derivative and a method for preparing anserine through the synthesized N (tau)-methyl-L-histidine derivative. According tothe method, raw materials are cheap and easy to obtain, the selectivity is good, and the yield is high; the operation is simple and practicable, the process is stable, the control is easy, the treatment after reaction is convenient, the product yield is good, the purity is high, and the preparation method can be economically and conveniently used for industrialized production.

Allylpalladium(II) histidylidene complexes and their application in Z-selective transfer semihydrogenation of alkynes

We have studied the use of amino acid histidine as a precursor for N-heterocyclic carbene (NHC) ligands. This natural amino acid possesses an imidazole substituent, which makes it an interesting NHC precursor that contains both an acid and an amino functi

Cysteine as a sustainable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: Biomimetic synthesis of l-ergothioneine in water

Biomass-derived cysteine was used as a sustainable sulfur source for the synthesis of rare sulfur-containing amino acids, such as l-ergothioneine (4), which might be a new vitamin, and various l- or d-2-thiohistidine compounds. Key in this simple, one-pot two-step procedure in water is a bromine-induced regioselective introduction of cysteine followed by a novel thermal cleavage reaction in the presence of thiols, a safer alternative to hazardous red phosphorus. Besides avoiding hazardous sulfur reagents, the new protecting-group-free approach reduces drastically the total number of steps, compared to described procedures. The main drawback, i.e. handling of liquid bromine as an activating and oxidizing reagent in water, was addressed by evaluating four alternative methods using in situ generation of bromine or HOBr, and first encouraging results are described.