Pipecolic acid

Pipecolic acid
Names
	Preferred IUPAC name Piperidine-2-carboxylic acid
Identifiers
CAS Number	3105-95-1 (2S) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17964 ;
ChemSpider	826 ;
ECHA InfoCard	100.007.835
EC Number	217-024-4;
KEGG	C00408 ;
MeSH	C031345
PubChem CID	849;
UNII	69374CKB33 ;
CompTox Dashboard (EPA)	DTXSID40862144 ;
	InChI InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) Key: HXEACLLIILLPRG-UHFFFAOYSA-N ; InChI=1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) Key: HXEACLLIILLPRG-UHFFFAOYAL;
	SMILES C1CCNC(C1)C(=O)O;
Properties
Chemical formula	C6H11NO2
Molar mass	129.15704
Appearance	white or colorless solid
Melting point	268 °C (514 °F; 541 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC₅H₉CO₂H. It is a carboxylic acid derivative of piperidine and, as such, an amino acid, although not one encoded genetically. Like many other α-amino acids, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid.

Its biosynthesis starts from lysine.^[1] CRYM, a taxon-specific protein that also binds thyroid hormones, is involved in the pipecolic acid pathway.

^ Gatto, Gregory J.; Boyne, Michael T.; Kelleher, Neil L.; Walsh, Christopher T. (2006). "Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster". Journal of the American Chemical Society. 128 (11): 3838–3847. doi:10.1021/ja0587603. PMID 16536560.

[1] Gatto, Gregory J.; Boyne, Michael T.; Kelleher, Neil L.; Walsh, Christopher T. (2006). "Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster". Journal of the American Chemical Society. 128 (11): 3838–3847. doi:10.1021/ja0587603. PMID 16536560.

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