Sarcosine

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Sarcosine
Skeletal formula of sarcosine
Names
Preferred IUPAC name
(Methylamino)acetic acid
Identifiers
3D model (JSmol)
3DMet
1699442
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.217 Edit this at Wikidata
EC Number
  • 203-538-6
2018
KEGG
MeSH Sarcosine
UNII
  • InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6) checkY
    Key: FSYKKLYZXJSNPZ-UHFFFAOYSA-N checkY
  • CNCC(O)=O
Properties
C3H7NO2
Molar mass 89.094 g·mol−1
Appearance White crystalline powder
Odor Odourless
Density 1.093 g/mL
Melting point 208 to 212 °C (406 to 414 °F; 481 to 485 K) experimental
Boiling point 195.1 °C (383.2 °F; 468.2 K) predicted
89.09 g L−1 (at 20 °C)
log P 0.599
Acidity (pKa) 2.36
Basicity (pKb) 11.64
UV-vismax) 260 nm
Absorbance 0.05
Thermochemistry
128.9 J K−1 mol−1
−513.50–−512.98 kJ mol−1
−1667.84–−1667.54 kJ mol−1
Related compounds
Related alkanoic acids
Related compounds
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Sarcosine, also known as N-methylglycine, or monomethylglycine, is the organic compound with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2, which can be obtained as a white, water-soluble powder. Like some other amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

Sarcosine is ubiquitous in biological materials. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications.

Sarcosine is sweet to the taste.[citation needed]

Biochemistry[edit]

Sarcosine is an intermediate and byproduct in glycine synthesis and degradation. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is an amino acid derivative that is naturally found in muscles and other body tissues. In the laboratory, it may be synthesized from chloroacetic acid and methylamine. Sarcosine is found naturally as an intermediate in the metabolism of choline to glycine.

Sarcosine, like the related compounds dimethylglycine (DMG) and trimethylglycine (TMG), is formed via the metabolism of nutrients such as choline and methionine, which both contain methyl groups used in a wide range of biochemical reactions. Sarcosine is rapidly degraded to glycine, which, in addition to its importance as a constituent of protein, plays a significant role in various physiological processes as a prime metabolic source of components of living cells such as glutathione, creatine, purines and serine. The concentration of sarcosine in blood serum of normal human subjects is 1.4 ± 0.6 micromolar.[1]

Surfactants[edit]

A variety of surfactants are produced from sarcosine.[2]

Clinical investigations[edit]

Sarcosine has been investigated in relation to schizophrenia. Early evidence suggests that intake of 2 g/day sarcosine as add-on therapy to certain antipsychotics (not clozapine[3] Sarcosine has been debated as a biomarker for prostate cancer cells.[4][5]

History[edit]

Sarcosine was first isolated and named by the German chemist Justus von Liebig in 1847.

Jacob Volhard first synthesized it in 1862 while working in the lab of Hermann Kolbe. Prior to the synthesis of sarcosine, it had long been known to be a hydrolysis product of creatine, a compound found in meat extract. Under this assumption, by preparing the compound with methylamine and monochloroacetic acid, Volhard proved that sarcosine was N-methylglycine.[6]

See also[edit]

References[edit]

  1. ^ Allen RH, Stabler SP, Lindenbaum J (November 1993). "Serum betaine, N,N-dimethylglycine and N-methylglycine levels in patients with cobalamin and folate deficiency and related inborn errors of metabolism". Metabolism. 42 (11): 1448–60. doi:10.1016/0026-0495(93)90198-W. PMID 7694037.
  2. ^ Holmberg, Krister (2019). "Surfactants". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–56. doi:10.1002/14356007.a25_747.pub2. ISBN 9783527306732. S2CID 242339510.
  3. ^ Lane HY, Huang CL, Wu PL, Liu YC, Chang YC, Lin PY, Chen PW, Tsai G (September 2006). "Glycine transporter I inhibitor, N-methylglycine (sarcosine), added to clozapine for the treatment of schizophrenia". Biological Psychiatry. 60 (6): 645–9. doi:10.1016/j.biopsych.2006.04.005. PMID 16780811. S2CID 42741531.
  4. ^ Struys EA, Heijboer AC, van Moorselaar J, Jakobs C, Blankenstein MA (May 2010). "Serum sarcosine is not a marker for prostate cancer". Annals of Clinical Biochemistry. 47 (Pt 3): 282. doi:10.1258/acb.2010.009270. PMID 20233752.
  5. ^ Pavlou M, Diamandis EP (July 2009). "The search for new prostate cancer biomarkers continues". Clinical Chemistry. 55 (7): 1277–9. doi:10.1373/clinchem.2009.126870. PMID 19478024.
  6. ^ Rocke, Alan J. (1993). "The Theory of Chemical Structure and the Structure of Chemical Theory". The Quiet Revolution: Hermann Kolbe and the Science of Organic Chemistry. Berkeley: University of California. pp. 239–64. ISBN 978-0-520-08110-9.