Anserine

Anserine is a dipeptide found in skeletal muscle of vertebrates.

Solid

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.|Anserine is a dipeptide comprised of a beta-alanine and a methylhistidine that is found in dietary red meat and has antioxidant activity.|A dipeptide containing BETA-ALANINE.

To a solution of ester 14 (18.8 mg, 53.0 μmol) in MeOH (1 mL) was basified with 1 M aqueous NaOH(>pH 11) and the mixture was stirred for 16 h at rt. Evaporation gave a residual gum that was dissolved in distilled H2O (1 mL) and the reaction mixture was acidified with 1 M aqueous HCl (N(alpha)-(3-((tert-Butoxycarbonyl)amino)propylcarbonyl)-N(tau)-methyl-L-histidine methyl ester (10 g, 28 mmol) was dissolved in 50 mL methanol and 20 mL water.6M hydrochloric acid (5 mL) was added at 20-30 C, and the mixture was heated to 40-50 C for 4 hours. TLC showed that the basic reaction was complete, and then neutralized to neutral with an anion exchange resin.Add 1M potassium hydroxide (30 mL) at 20-30 C, stir at this temperature for 8 hours, complete the basic reaction by TLC, neutralize to neutral by adding cation exchange resin, concentrate after filtration, and the obtained crude product is beaten with ethanol and filtered. After drying, the white solid goose carnosine was 6.2 g, the molar yield was 92%, and the purity was 97%.Add 6M hydrochloric acid (5 mL) at 20-30 C, and warm to 40-50 C for 4 hours. TLC showed that the basic reaction was complete, neutralized by neutralization with anion exchange resin, concentrated after filtration, and the obtained crude product was beaten with ethanol and filtered. After drying, the white solid goose carnosine was 6.4 g, the molar yield was 95%, and the purity was 97%.1H NMR (400MHz, D2O) delta 7.45 (d, J = 1.2 Hz, 1H), 6.67 (d, J = 1.2 Hz, 1H), 4.35 (dd, J = 9.5, 4.8 Hz, 1H), 3.52 (s, 3H), 3.17 - 3.00 (m, 1H), 2.94 (t, J = 6.7 Hz, 2H), 2.83 (dd, J = 15.5, 9.5 Hz, 1H), 2.53 - 2.35 (m, 2H).Add 1M hydrochloric acid (25 mL) at 20-30 C. Warm up to 40-50 C and stir for 8 hours. TLC shows that the basic reaction is complete, Neutralize to neutral by adding anion exchange resin, Concentrated after filtration, The obtained crude product is beaten with ethanol, After filtration, the white solid goose carnosine 5.1g was dried. The molar yield was 93% and the purity was 97%.Add 10% Pd-C (1g) at 20-30 C, stir and hydrogenate at this temperature for 2 hours, complete the basic reaction by TLC, concentrate after filtration, and the crude product obtained is beaten with ethanol, filtered and dried to obtain white goose carnosine. 4.9 g, molar yield 90%, purity 97%.

Molecular Weight:240.26
XLogP3:-4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:240.12224039
Monoisotopic Mass:240.12224039
Topological Polar Surface Area:110
Heavy Atom Count:17
Complexity:285
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes