3-Methylhistidine

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3-Methylhistidine
(2S)-2-amino-3-(3-methylimidazol-4-yl)propanoic acid.svg
Names
Preferred IUPAC name
(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Identifiers
3D model (JSmol)
83651
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.095 Edit this at Wikidata
EC Number
  • 206-704-6
1568650
KEGG
UNII
  • InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1
    Key: JDHILDINMRGULE-LURJTMIESA-N
  • CN1C=NC=C1CC(C(=O)O)N
Properties
C7H11N3O2
Molar mass 169.184
200 mg/mL at 25 °C[1][2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Methylhistidine (3-MH) is a post-translationally modified amino acid which is excreted in human urine.[1][2] Urinary concentration of 3-methylhistidine is a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury.[1][3][4] Urinary 3-methylhistidine concentrations are also elevated from consumption of soy-based products and meat, particularly chicken.[1]

Biochemistry[edit]

3-Methylhistidine is a metabolic product that is produced in the body via the enzymatic methylation of histidine during peptide bond synthesis and the methylation of actin and myosin.[1][2]

Detection in body fluids[edit]

The normal concentration of 3-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 3.63–69.27 micromoles per millimole (μmol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15–20 μmol/mmol of creatinine.[1] The average concentration of 3-methylhistidine in human blood plasma has been detected and quantified at 2.85 micromolar (μM) with a range of 0.0–5.9 μM.[1] The average concentration of 3-methylhistidine in human cerebrospinal fluid (CSF) has been detected and quantified at 3.82 μM with a range of 1.39–6.25 μM.[1]

References[edit]

  1. ^ a b c d e f g h "3-Methylhistidine". HMDB Version 4.0. Human Metabolome Database. 20 December 2017. Retrieved 25 December 2017.
  2. ^ a b c "3-Methyl-L-histidine". PubChem Compound. United States National Library of Medicine – National Center for Biotechnology Information. 23 December 2017. Retrieved 25 December 2017.
  3. ^ Chinkes DL (September 2005). "Methods for measuring tissue protein breakdown rate in vivo". Current Opinion in Clinical Nutrition and Metabolic Care. 8 (5): 534–537. doi:10.1097/01.mco.0000170754.25372.37. PMID 16079625. S2CID 8318490.
  4. ^ Holm L, Kjaer M (September 2010). "Measuring protein breakdown rate in individual proteins in vivo". Current Opinion in Clinical Nutrition and Metabolic Care. 13 (5): 526–531. doi:10.1097/MCO.0b013e32833c3c64. PMC 3008417. PMID 20616712.