C9625

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C9625

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L-Carnosine

~99%, crystalline

Synonym:β-Alanyl-L-histidine
Amino Acid Sequence:β-Ala-His
CAS Number:305-84-0
Linear Formula:C9H14N4O3
Molecular Weight:226.23
Beilstein Registry Number:87671
EC Number:206-169-9
MDL number:MFCD00005207
PubChem Substance ID:24893178

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Description

Biochem/physiol ActionsDipeptide with potent antioxidant and antiglycation activity; blocks nonenzymatic glycosylation and protein cross-linking induced by reactive aldehydes.
 L-Carosine is a dipeptide found at millimolar concentration in brain, muscle and the lens of the eye. In model systems it is a potent antioxidant that scavenges oxygen free radicals and transition metal ions. It blocks protein-protein and protein-DNA cross-links induced by hypochlorite anions and toxic aldehydes such as acetaldehyde, formaldehyde, and malondialdehyde, the primary product of lipid peroxidation. It also inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars and inhibits the formation of toxic advanced glycation end products (AGE). These activities make it of interest in studies of aging, atherosclerosis, Alzheimer's disease, and the secondary effects of diabetes.

Properties

assay~99%
formcrystalline
mp253 °C (dec.)(lit.)
Gene Informationhuman ... CA1(759), CA2(760)
storage temp.−20°C

Safety

Personal Protective EquipmentEyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
WGK Germany2
RTECSMS3080000

References

referenceHipkiss, A.R., et al., Pluripotent protective effects of carnosine, a naturally occurring dipeptide. Ann. N.Y. Acad. Sci. 854, 37-53, (1998)
 Hipkiss, A.R., Could carnosine or related structures suppress Alzheimer's disease? J. Alzheimers Dis. 11, 229-240, (2007)
 Aldini, G., et al., Carnosine and related dipeptides as quenchers of reactive carbonyl species: from structural studies to therapeutic perspectives. Biofactors 24, 77-87, (2005)
 Yan, H., and Harding, J.J., Carnosine inhibits modifications and decreased molecular chaperone activity of lens alpha-crystallin induced by ribose and fructose 6-phosphate. Mol. Vis. 12, 205-214, (2006)
 Szwergold, B.S., Carnosine and anserine act as effective transglycating agents in decomposition of aldose-derived Schiff bases. Biochem. Biophys. Res. Commun. 336, 36-41, (2005)
MerckMerck 13,1863
BeilsteinBeil. 25,IV,4381
 FT-IR 2 (3), 3519:C / FT-IR 1 (2), 622:A / FT-NMR 1 (3), 86:A / IR-Spectra (3), 1222:C / NMR-Reference 2 (2), 494:D / RegBook 1 (2), 2361:O / Sigma FT-IR 1 (1), 318:A / Structure Index 1, 374:A:4