331-38-4

Usage

InChI:InChI=1/C10H16N4O3/c1-14-5-7(12-6-14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1

Upstream product

• 890306-83-9 (S)-methyl 2-(benzyloxycarbonylamino)-3-(1-methyl-1H-imidazol-4-yl)propanoate 
• 17289-26-8 1-methyl-1H-imidazole-4-carbaldehyde 
• 57519-09-2 (S)-methyl 2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoate 
• 69614-04-6 S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 
• 7389-87-9 L-histidine methyl ester dihydrochloride 
• 69618-95-7 (S)-7-(methoxycarbonyl)-2-methyl-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c] pyrimidin-2-ium iodide 
• 200926-96-1 (S)-1-carboxy-2-(1-methyl-1H-imidazol-4-yl)ethanaminium chloride 

Relevant academic research and scientific papers

Preparation method of balenine intermediate and balenine, and balenine intermediate

The invention provides a balenine intermediate shown as a formula (II) and a preparation method thereof, and the method comprises the following steps: in the presence/absence of alkali, condensing a compound (III) with a compound (IV) in a solvent to obtain the compound (II). The method has the advantages of simple operation, easy implementation, stable process, easy control, convenient post-reaction treatment, good product yield and high quality, and can be economically and conveniently used for industrial production, and the reaction route is as shown in the specification.The invention also provides a method for preparing balenine from the balenine intermediate.

Preparation methods of whale carnosine and intermediate thereof

The invention provides two preparation methods of whale carnosine and a preparation method of an intermediate for synthesizing the whale carnosine. The two preparation methods of the whale carnosine and the preparation method of the intermediate for synthesizing the whale carnosine, provided by the invention, have the advantages of simple and easy operation, stable process, easy control, convenient treatment after reaction, good product yield and high purity and can be economically and conveniently used for industrial production.

Preparation methods of two kinds of anserine and immediate of anserine

The invention provides preparation methods of two kinds of anserine and a preparation method of a synthetic anserine intermediate. The preparation methods are simple to operate, easy to implement, stable in process, easy to control, convenient for reaction post-treatment, good in product yield, high in purity and capable of being economically and conveniently used for industrial production.

Carnosine protects cardiac myocytes against lipid peroxidation products

Endogenous histidyl dipeptides such as carnosine (β-alanine-l-histidine) form conjugates with lipid peroxidation products such as 4-hydroxy-trans-2-nonenal (HNE and acrolein), chelate metals, and protect against myocardial ischemic injury. Nevertheless, it is unclear whether these peptides protect against cardiac injury by directly reacting with lipid peroxidation products. Hence, to examine whether changes in the structure of carnosine could affect its aldehyde reactivity and metal chelating ability, we synthesized methylated analogs of carnosine, balenine (β-alanine-Nτ-methylhistidine) and dimethyl balenine (DMB), and measured their aldehyde reactivity and metal chelating properties. We found that methylation of Nτ residue of imidazole ring (balenine) or trimethylation of carnosine backbone at Nτ residue of imidazole ring and terminal amine group dimethyl balenine (DMB) abolishes the ability of these peptides to react with HNE. Incubation of balenine with acrolein resulted in the formation of single product (m/z 297), whereas DMB did not react with acrolein. In comparison with carnosine, balenine exhibited moderate acrolein quenching capacity. The Fe2+ chelating ability of balenine was higher than that of carnosine, whereas DMB lacked chelating capacity. Pretreatment of cardiac myocytes with carnosine increased the mean lifetime of myocytes superfused with HNE or acrolein compared with balenine or DMB. Collectively, these results suggest that carnosine protects cardiac myocytes against HNE and acrolein toxicity by directly reacting with these aldehydes. This reaction involves both the amino group of β-alanyl residue and the imidazole residue of l-histidine. Methylation of these sites prevents or abolishes the aldehyde reactivity of carnosine, alters its metal-chelating property, and diminishes its ability to prevent electrophilic injury.

Preparation method of N(pi)-methyl-L-histidine derivative and application thereof to synthesis of whale carnosine

The invention relates to a preparation method of an N(pi)-methyl-L-histidine derivative and a method for preparing anserine from the synthesized N(pi)-methyl-L-histidine derivative. By the preparationmethod, raw materials are cheap and easy to obtain, the selectivity is good and the yield is high; the operation is simple and easy to implement, a technology is stable, the control is easy, treatment after a reaction is convenient, the product yield is good, the purity is high, and the preparation method can be economically and conveniently applied to industrial production.

Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction

A concise synthesis of anserine and related compounds was accomplished by Et-DuPhos-Rh-catalyzed asymmetric hydrogenation of dehydrohistidine derivatives in 2,2,2-trifluoroethanol, which played a key role in improving the yield and selectivity.