584-85-0

Anserine, a methylated form of Carnosine, is an orally active, natural Histidine-containing dipeptide found in skeletal muscle of vertebrates. Anserine is not cleaved by serum carnosinase and act as biochemical buffers, chelators, antioxidants, and anti-glycation agents. Anserine improves memory functions in Alzheimer's disease (AD)-model mice[1][2].

ChEBI: Anserine is a dipeptide comprising of beta-alanine and 3-methyl-L-histidine units. It has a role as an animal metabolite and a mouse metabolite. It is a beta-alanine derivative and a dipeptide. It is a tautomer of an anserine zwitterion.

The general procedure for the synthesis of (S)-2-(3-aminopropionamido)-3-(1-methyl-1H-imidazol-5-yl)propionic acid, using the compound (CAS: 952739-81-0) as a starting material, was as follows: to a solution of methanol (1 mL) containing the ester 14 (18.8 mg, 53.0 μmol), 1 M aqueous sodium hydroxide was added to adjust the pH to >11. The reaction was carried out by stirring the reaction mixture for 16 h at room temperature. reaction mixture was stirred for 16 h at room temperature. Upon completion of the reaction, the solvent was removed by evaporation to give a colloidal residue. This residue was dissolved in distilled water (1 mL) and the reaction mixture was subsequently acidified with 1 M aqueous hydrochloric acid.

Human Endogenous Metabolite

Store at 4°C, protect from light

Crystallise anserine from aqueous EtOH. It is hygroscopic and is best stored as the nitrate salt (see below). Purify it by shaking the nitrate salt with Dowex 3 (x4 free base) and washing with H2O, evaporating the filtrate and removing H2O by 3 distillations with 10mL of propan-2-ol. Dissolve the crystals in MeOH and add H2O dropwise until one phase is obtained and cool. Dry the crystals at 60o over P2O5 in a vacuum. The picrate has m 145o (from H2O). [Rinderknecht et al. J Org Chem 29 1968 1964, Beilstein 25 II 408, 25 IV 4383.]

[1] Boldyrev AA, et al. The histidine-containing dipeptides, carnosine and anserine: distribution, properties and biological significance. Adv Enzyme Regul. 1990;30:175-94. DOI:10.1016/0065-2571(90)90017-v
[2] Jun Kaneko, et al. Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AβPPswe/PSEN1dE9 Alzheimer's-model mice. Sci Rep. 2017 Oct 3;7(1):12571. DOI:10.1038/s41598-017-12785-7