36097-48-0

Usage

Uses

Used in Pharmaceutical Industry:
AC-HIS-OME is used as a pharmaceutical compound for its potential therapeutic effects. As a derivative of L-Histidine, it may have implications in the treatment of various health conditions, including those related to the immune system and cellular metabolism.
Used in Nutritional Supplements:
AC-HIS-OME is used as an ingredient in nutritional supplements for its potential benefits in enhancing overall health and well-being. Its role in cellular metabolism and immune function makes it a valuable addition to dietary supplements.
Used in Research and Development:
AC-HIS-OME is used as a research compound for studying the properties and potential applications of L-Histidine and its derivatives. This can lead to the development of new drugs, therapies, and supplements that leverage the unique characteristics of AC-HIS-OME.
Used in Cosmetics Industry:
AC-HIS-OME may be used as an ingredient in the cosmetics industry for its potential benefits in skin health and rejuvenation. Its role in cellular metabolism could contribute to the development of products that promote skin regeneration and overall skin health.

InChI:InChI=1/C9H13N3O3/c1-6(13)12-8(9(14)15-2)3-7-4-10-5-11-7/h4-5,8H,3H2,1-2H3,(H,10,11)(H,12,13)/t8-/m0/s1

Upstream product

• 71-00-1 L-histidine 
• 75-36-5 acetyl chloride 
• 71-00-1 L-histidine 
• 67-56-1 methanol 
• 917484-74-3 (1R,2R)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane 
• 1499-46-3 L-Histidine methyl ester 
• 2497-02-1 N-acetyl-L-histidine 

Downstream Products

• 154061-60-6 N^α-Acetyl-N^τ-(p-nitrophenyl)-L-histidine methyl ester 
• 1643359-99-2 N-α-acetyl-2-(4-trifluoromethylphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-29-5 C₃₀H₂₅F₆N₃O₃ 
• 1643360-02-4 N-α-acetyl-2-(3-trifluoromethylphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-03-5 N-α-acetyl-2-(2-trifluoromethylphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-04-6 N-α-acetyl-2-(4-cyanophenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-05-7 N-α-acetyl-2-(4-chlorophenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-06-8 N-α-acetyl-2-phenyl-1-benzyl-L-histidine methyl ester 
• 1643360-07-9 N-α-acetyl-2-(4-tert-butylphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-08-0 N-α-acetyl-2-(4-methylphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-09-1 N-α-acetyl-2-(4-methoxyphenyl)-1-benzyl-L-histidine methyl ester 
• 1643360-11-5 N-α-acetyl-2-biphenyl-1-benzyl-L-histidine methyl ester 
• 1643360-13-7 N-α-acetyl-2-(2-napthyl)-1-benzyl-L-histidine methyl ester 
• 1643360-00-2 N-α-acetyl-2-(4-trifluoromethylphenyl)-L-histidine methyl ester 

Relevant academic research and scientific papers

Determination of Acid Dissociation Constants of Histidine-Containing Peptides by Proton Magnetic Resonance Spectroscopy

The acid dissociation constant of the imidazolium ring of the decapeptide luliberin has been determined by 1H NMR-followed titration in D2O.The normal procedure for the analysis of the titration curve, i. e. direct use of the Henderson-Haselbalch equation, is still applicable in this case, but for more complex peptides a modified calculation procedure is proposed.Results obtained when both methods were applied to luliberin are compared.The influence of D2O when used as the solvent in this type of determination has been studied using Nα-acetyl-L-histidine methyl ester as a model compound.The difference between the acid dissociation constant of this molecule determined in H2O and in D2O implies that a correction of -0.25 unit is needed for those pKa values calculated by plotting the chemical shifts in D2O vs the apparent pH meter readings.The pKa found for Nα-acetyl-L-histidine methyl ester, 6.30 +/- 0.04, can be taken as a standard value for histidine-containing peptides.

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.

Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides

For application in drug discovery and biomedicine, it is crucial to develop new biocompatible methods to modify polypeptides. Herein, a visible-light-induced photoredox trifluoromethylation of tryptophan-containing peptides is reported. Under a mild, biocompatible, and straightforward condition, this strategy could incorporate the trifluoromethyl group into tryptophan residue with excellent chemo- and site-selectivity. The use of lower photocatalyst loading in 2 mol-% and cheap CF3SO2Na salt represents a great catalytic activity and economic CF3 source. This direct trifluoromethylation strategy allows the ready study of fluorinated peptides exploiting 19F-NMR. Additionally, the development of this protocol enables the study of biochemical systems and potentially modulates the function of biomolecules. Careful mechanistic studies (Stern-Volmer fluorescence quenching, EPR, and radical inhibition/trapping experiments) indicate that the reaction would proceed with a radical–radical cross-coupling procedure.

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

Histidine (His) carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for site-selective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remains one of the most difficult challenges in peptide chemistry. Herein, we report peptide modification via radical-mediated chemoselective C-H alkylation of histidine using C4-alkyl-1,4-dihydropyridine (DHP) reagents under visible-light-promoted conditions. The method exploits the electrophilic reactivity of the imidazole ring via a Minisci-type reaction pathway. This method exhibits an exceptionally broad scope for both peptides and DHP alkylation reagents. Its utility has been demonstrated in a series of important peptide drugs, complex natural products, and a small protein. Distinct from N-substitution reactions, the unsubstituted nitrogen groups of the modified imidazole ring are conserved in the C-H alkylated products.

Nanomole-scale assignment of configuration for primary amines using a kinetic resolution strategy

The absolute configurations of primary amines were assigned using a kinetic resolution strategy with Mioskowski's enantioselective 1-(R,R) and 2-(S,S) acylating agents. A simple mnemonic was developed to determine the configuration. A pseudoenantiomeric pair of reagents, 1-(R,R) and 2-(S,S)-d 3, was prepared and used to assay primary amines on a micromolar scale. The ESI-MS readout of the resulting acetamide products reproduced the selectivity factors from kinetic experiments. The method can be used on mixtures of amines and was validated with amine samples as small as 50 nmol.

Synthesis and catalytic activity of histidine-based NHC ruthenium complexes

Main-chain C,N-protected histidine has been successfully alkylated at both side-chain nitrogens. The corresponding histidinium salt was metallated with ruthenium(ii) by a transmetalation procedure, thus providing histidine-derived NHC ruthenium complexes. These bio-inspired complexes show appreciable activity in the catalytic transfer hydrogenation of ketones. The Royal Society of Chemistry 2011.

Synthesis of 5-arylhistidines via a Suzuki-Miyaura cross-coupling

Microwave irradiation efficiently promoted the Suzuki-Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of histidines substituted at position 5 of the imid

ANTI-ODOR COMPOSITIONS AND THERAPEUTIC USE

This application discloses a composition comprising a malodor compound and an anti-odor ingredient effective for reducing the presence or production of malodor. The composition may be topically applied to a subject and is useful for cosmetic conditions, pharmaceutical indications, or other objectives.

Catalytic specificity exhibited by p-sulfonatocalix[n]arenes in the methanolysis of N-acetyl-L-amino acids

Specific acid catalysis of p-sulfonatocalix[n]arenes (n = 4, Calix-S4; n = 6, Calix-S6; n = 8, Calix-S8) was observed in the alcoholysis of N-acetyl-L-amino acids in methanol. The methanolysis rates of basic amino acid substrates (His, Lys, and Arg) were