Acetylcarnosine

Acetylcarnosine
Names
IUPAC name
(S)-2-(3-Acetamidopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid
Other names
N-(N-Acetyl-β-alanyl)histidine; N-Acetyl-L-carnosine; N-Acetylcarnosine
Identifiers
3D model (JSmol)
Abbreviations NAC
ChemSpider
ECHA InfoCard 100.054.640 Edit this at Wikidata
UNII
  • InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m0/s1 checkY
    Key: BKAYIFDRRZZKNF-VIFPVBQESA-N checkY
  • InChI=1/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m0/s1
    Key: BKAYIFDRRZZKNF-VIFPVBQEBE
  • O=C(NCCC(=O)N[C@H](C(=O)O)Cc1c[nH]cn1)C
Properties
C11H16N4O4
Molar mass 268.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Acetylcarnosine (NAC) (not to be confused with N-Acetylcysteine, which is also abbreviated "NAC") is a naturally occurring[1] compound chemically related to the dipeptide carnosine. The NAC molecular structure is identical to carnosine with the exception that it carries an additional acetyl group. The acetylation makes NAC more resistant to degradation by carnosinase, an enzyme that breaks down carnosine to its constituent amino acids, beta-alanine and histidine.[2]

  1. ^ Cite error: The named reference Boldyrev & Abe was invoked but never defined (see the help page).
  2. ^ Pegova A, Abe H, Boldyrev A (December 2000). "Hydrolysis of carnosine and related compounds by mammalian carnosinases". Comp. Biochem. Physiol. B. 127 (4): 443–6. doi:10.1016/S0305-0491(00)00279-0. PMID 11281261.