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{{chembox |
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| verifiedrevid = 290480021 |
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|ImageFile=Piperidine-2-carboxylic acid.png |
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| verifiedrevid = 445012529 |
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|ImageSize=216px |
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| ImageFile = Structural formula of pipecolic acid.svg |
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|IUPACName=piperidine-2-carboxylic acid |
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| ImageSize = 216px |
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|OtherNames= |
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| PIN = Piperidine-2-carboxylic acid |
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|Section1= {{Chembox Identifiers |
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| OtherNames = |
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| CASNo=3105-95-1 |
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|Section1={{Chembox Identifiers |
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| CASOther= |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem=849 |
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| CASNo = 3105-95-1 |
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| SMILES=C1CCNC(C1)C(=O)O |
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| CASNo_Comment = (2''S'') |
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| MeSHName=pipecolic+acid |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|Section2= {{Chembox Properties |
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| UNII = 69374CKB33 |
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| Formula=C<sub>6</sub>H<sub>11</sub>NO<sub>2</sub> |
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| PubChem = 849 |
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| MolarMass=129.15704 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| Appearance= |
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| KEGG = C00408 |
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| SMILES = C1CCNC(C1)C(=O)O |
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| MeltingPt= |
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| EINECS = 217-024-4 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Solubility= |
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| ChemSpiderID = 826 |
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| InChI = 1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) |
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|Section3= {{Chembox Hazards |
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| InChIKey = HXEACLLIILLPRG-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| FlashPt= |
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| StdInChI = 1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) |
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| Autoignition= |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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| StdInChIKey = HXEACLLIILLPRG-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = C031345 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 17964 |
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}} |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>11</sub>NO<sub>2</sub> |
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| MolarMass = 129.15704 |
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| Appearance = white or colorless solid |
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| Density = |
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| MeltingPtC = 268 |
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|Section3={{Chembox Hazards |
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'''Pipecolic acid''' (piperidine-2-carboxylic acid) is a small organic molecule which accumulates in ]. It is the carboxylic acid of ]. |
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'''Pipecolic acid''' (piperidine-2-carboxylic acid) is an organic compound with the formula HNC<sub>5</sub>H<sub>9</sub>CO<sub>2</sub>H. It is a carboxylic acid derivative of ] and, as such, an ], although not one encoded genetically. Like many other ]-]s, pipecolic acid is chiral, although the S-stereoisomer is more common. It is a colorless solid. |
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Its biosynthesis starts from ].<ref>{{cite journal |doi=10.1021/ja0587603|title=Biosynthesis of Pipecolic Acid by RapL, a Lysine Cyclodeaminase Encoded in the Rapamycin Gene Cluster|year=2006|last1=Gatto|first1=Gregory J.|last2=Boyne|first2=Michael T.|last3=Kelleher|first3=Neil L.|last4=Walsh|first4=Christopher T.|journal=Journal of the American Chemical Society|volume=128|issue=11|pages=3838–3847|pmid=16536560}}</ref> ], a taxon-specific protein that also binds ]s, is involved in the pipecolic acid pathway. |
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It can be associated with some forms of ].<ref name="pmid15944906">{{cite journal |author=Plecko B, Hikel C, Korenke GC, ''et al.'' |title=Pipecolic acid as a diagnostic marker of pyridoxine-dependent epilepsy |journal=Neuropediatrics |volume=36 |issue=3 |pages=200–5 |year=2005 |pmid=15944906 |doi=10.1055/s-2005-865727}}</ref> |
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==Medicine== |
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], a taxon-specific ] protein that also binds ]s, is involved in the pipecolic acid pathway. |
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It accumulates in ]. Elevation of pipecolic acid can be associated with some forms of ], such as ].<ref name="pmid15944906">{{cite journal |vauthors=Plecko B, Hikel C, Korenke GC, etal |title=Pipecolic acid as a diagnostic marker of pyridoxine-dependent epilepsy |journal=Neuropediatrics |volume=36 |issue=3 |pages=200–5 |year=2005 |pmid=15944906 |doi=10.1055/s-2005-865727}}</ref><ref name="pmid35053812">{{cite journal | vauthors = Kaminiów K, Pająk M, Pająk R, Paprocka J | title = Pyridoxine-Dependent Epilepsy and Antiquitin Deficiency Resulting in Neonatal-Onset Refractory Seizures | journal = Brain Sciences | volume = 12 | issue = 1 | date = December 2021 | page = 65 | pmid = 35053812 | pmc = 8773593 | doi = 10.3390/brainsci12010065 | url = | doi-access = free }}</ref> |
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==Occurrence and reactions== |
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Pipecolic acid was identified in the ].<ref>{{cite journal |last1= Kvenholden |first1= Keith A. |last2= Lawless |first2= James G. |last3= Ponnamperuma |first3 = Cyril |year= 1971 |month= February |title= Nonprotein Amino Acids in the Murchison Meteorite |journal= Proceedings of the National Academy of Sciences |volume= 68 |issue= 2 |pages= 486–490 |pmc= 388966 |accessdate= August 4, 2011 }}</ref> |
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Like most amino acids, pipecolic acid is a chelating agent. One complex is Cu(HNC<sub>5</sub>H<sub>9</sub>CO<sub>2</sub>)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>.<ref>{{cite journal |doi=10.1016/0957-4166(95)00400-9|title=Convenient resolution of (±)-piperidine-2-carboxylic acid ((±)-pipecolic acid) by separation of palladium(II) diastereomers containing orthometallated (S)-(−)-1-[1-(dimethylamino)ethyl]naphthalene|year=1995|last1=Hockless|first1=David C.R.|last2=Mayadunne|first2=Renuka C.|last3=Wild|first3=S.Bruce|journal=Tetrahedron: Asymmetry|volume=6|issue=12|pages=3031–3037}}</ref> |
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Pipecolic acid was identified in the ].<ref>{{cite journal |last1= Kvenholden |first1= Keith A. |last2= Lawless |first2= James G. |last3= Ponnamperuma |first3 = Cyril |date=February 1971 |title= Nonprotein Amino Acids in the Murchison Meteorite |journal= Proceedings of the National Academy of Sciences |volume= 68 |issue= 2 |pages= 486–490 | doi = 10.1073/pnas.68.2.486 |pmc= 388966 |pmid=16591908|bibcode= 1971PNAS...68..486K |doi-access= free }}</ref> |
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==References== |
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It also occurs in the leaves of the genus '']'', a tree from South America.<ref>{{cite journal | last1 = Kite | first1 = GC | last2 = Cardoso | first2 = D | last3 = Lewis | first3 = GP | last4 = Zartman | first4 = CE | last5 = de Queiroz | first5 = LP | last6 = Veitch | first6 = NC | year = 2015 | title = Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume | journal = Phytochemistry | volume = 116 | pages = 198–202 | doi = 10.1016/j.phytochem.2015.02.026 | pmid = 25817832| bibcode = 2015PChem.116..198K }}</ref> |
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==See also== |
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==See also== |
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==References== |
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