2-Methylserine

2-Methylserine
Names
	IUPAC name α-methyl-serine
	Systematic IUPAC name 2-Amino-3-hydroxy-2-methylpropanoic acid
Identifiers
CAS Number	D/L: 5424-29-3 ; L: 16820-18-1 ;
3D model (JSmol)	D/L: Interactive image; L: Interactive image;
ChEBI	D/L: CHEBI:134206 ;
ChEMBL	D/L: ChEMBL539702 ;
ChemSpider	D/L: 85112 ;
ECHA InfoCard	100.024.150
KEGG	D/L: C02115;
MeSH	2-methylserine
PubChem CID	D/L: 94309; L: 7000050;
UNII	D/L: CZ8HQ2F53F ;
CompTox Dashboard (EPA)	D/L: DTXSID001346506 ;
	InChI InChI=1S/C4H9NO3/c1-4(5,2-6)3(7)8/h6H,2,5H2,1H3,(H,7,8) Key: CDUUKBXTEOFITR-UHFFFAOYSA-N ; L: InChI=1S/C4H9NO3/c1-4(5,2-6)3(7)8/h6H,2,5H2,1H3,(H,7,8)/t4-/m0/s1 Key: CDUUKBXTEOFITR-BYPYZUCNSA-N;
	SMILES D/L: CC(CO)(C(=O)O)N; L: C[C@](CO)(C(=O)O)N;
Properties
Chemical formula	C4H9NO3
Molar mass	119.120 g·mol−1
Solubility in water	soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Methylserine is a non-proteinogenic amino acid that is structurally similar to serine. Like serine, it is polar, and therefore soluble in water. It differs structurally from serine by the presence of a methyl group on the backbone carbon.

2-Methylserine is one of the amino acids produced by an unpublished volcanic-spark discharge experiment conducted by Stanley Miller in the early 1950s. However, the presence of this and many other organic compounds was not discovered until Jeffrey Bada et al. re-analyzed the contents of the vials from Miller's experiment in 2008.^[1]

References

^ Johnson, Adam P.; Cleaves, H. James; Dworkin, Jason P.; Glavin, Daniel P.; Lazcano, Antonio; Bada, Jeffrey L. (2008-10-17). "The Miller Volcanic Spark Discharge Experiment". Science. 322 (5900): 404. Bibcode:2008Sci...322..404J. doi:10.1126/science.1161527. ISSN 0036-8075. PMID 18927386.

References

Further reading