Anserine

Anserine
Names
Systematic IUPAC name
(Z)-N-(3-Amino-1-hydroxypropylidene)-3-methyl-L-histidine
Other names
beta-Alanyl-3-methyl-L-histidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.679
KEGG
UNII
  • InChI=1S/C10H16N4O3/c1-14-6-12-5-7(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 Y
    Key: MYYIAHXIVFADCU-QMMMGPOBSA-N Y
  • InChI=1/C10H16N4O3/c1-14-6-12-5-7(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
    Key: MYYIAHXIVFADCU-QMMMGPOBBJ
  • O=C(O)[C@@H](NC(=O)CCN)Cc1cncn1C
Properties
C10H16N4O3
Molar mass 240.25904 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine. Anserine is a derivative of carnosine, which has been methylated.

Anserine has biological activities similar to those of carnosine, including buffering activity, antioxidant properties, metal ion chelation, and anti-aggregation effects. Both anserine and carnosine chelate copper. Because of its methylation, anserine is more stable in serum and resistant to degradation than carnosine. Compared with carnosine, anserine have a higher antioxidant capacity.

Anserine can be found in the skeletal muscle and brain of mammals and birds. Anserine is also found in human kidney.

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04.

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