Pipecolic acid
| Structural formula | |||||||||||||||||||
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| Simplified structural formula without stereochemistry | |||||||||||||||||||
| General | |||||||||||||||||||
| Surname | Pipecolic acid | ||||||||||||||||||
| other names |
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| Molecular formula | C 6 H 11 NO 2 | ||||||||||||||||||
| Brief description |
White dust |
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| properties | |||||||||||||||||||
| Molar mass | 129.16 g · mol -1 | ||||||||||||||||||
| Physical state |
firmly |
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| density |
1.04 g cm −3 |
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| Melting point |
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| pK s value |
2.36 (racemate) |
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| solubility |
soluble in water |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Pipecolic acid , also piperidine-2-carboxylic acid , is a non-proteinogenic amino acid in its natural L form . It arises from L- lysine either as an intermediate stage in the breakdown of the amino acid or via α- deamination with subsequent cyclization and reduction .
Isomers
Pipecolic acid has a stereocenter , so it is optically active and there are two enantiomers : L -pipecolic acid [synonym: ( S ) -pipecolic acid] and the mirror-image D -pipecolic acid [synonym: ( R ) -pipecolic acid]. A 1: 1 mixture of D- and L -form is called a racemate or DL -pipecolic acid.
| Isomers of pipecolic acid | ||
| Surname | L -pipecolic acid | D -pipecolic acid |
| other names | ( S ) -pipecolic acid (-) - pipecolic acid |
( R ) -pipecolic acid (+) - pipecolic acid |
| Structural formula |
-Pipecolic_acid.svg)
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-Pipecolic_acid.svg)
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| CAS number | 3105-95-1 | 1723-00-8 |
| 535-75-1 (racemate) | ||
| EC number | 221-462-1 | 217-024-4 |
| 208-616-3 (racemate) | ||
| ECHA info card | 100.019.511 | 100.015.477 |
| 100.007.835 (racemate) | ||
| PubChem | 439227 | 736316 |
| 849 (racemate) | ||
| Wikidata | Q27104171 | Q27104476 |
| Q7197255 (racemate) | ||
Occurrence
Pipecolic acid has been found in various microorganisms , plants and animals. In plants, pipecolic acid plays an important role as a regulator of plant resistance reactions. It was also detected in the Murchison meteorite .
Extraction and presentation
The synthesis of the natural, non-proteinogenic racemic pipecolic acid has long been known. One synthesis variant is the catalytic reduction of α- picolinic acid and subsequent racemate separation by means of fractional crystallization with tartaric acid . The naturally occurring ( S ) - enantiomer can be represented by different cyclization reactions starting from ( S ) -lysine. More recently, further, both diastereoselective and enantioselective synthesis variants have been described.
use
The determination of pipecolic acid is used in medical diagnostics for:
- neonatal seizures or if pyridoxine- dependent epilepsy is suspected (determined by gas chromatography / mass spectrometry )
- Suspected Zellweger Syndrome
Individual evidence
- ↑ a b c d e data sheet Pipecolinic acid, 98% from Sigma-Aldrich , accessed on January 28, 2016 ( PDF ).
- ^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2014, ISBN 978-0-323-29060-9 , pp. 281 ( limited preview in Google Book search).
- ↑ a b Entry on piperidinecarboxylic acids. In: Römpp Online . Georg Thieme Verlag, accessed on January 29, 2016.
- ↑ Entry on Pipecolic acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on January 29, 2016.
- ↑ Shmuel Yannai: Dictionary of Food Compounds with CD-ROM, Second Edition . CRC Press, 2012, ISBN 978-1-4200-8352-1 , pp. 1602 ( limited preview in Google Book Search).
- ↑ Spektrum.de: L-Pipecolinsäure - Lexikon der Biologie , accessed on January 28, 2016.
- ^ Gerhard Habermehl, Peter E. Hammann: Naturstoffchemie - An introduction . Springer-Verlag, 2013, ISBN 978-3-662-08929-3 , pp. 152 ( limited preview in Google Book search).
- ↑ H. Michl: About the occurrence of pipecolic acid in animal poisons. In: Monthly magazine for chemistry. 88, 1957, p. 701, doi : 10.1007 / BF00901355 .
- ↑ dfg.de: DFG GEPRIS - Metabolism and signal transduction of the plant immune signal pipecolic acid , accessed on January 28, 2016.
- ↑ KA Kvenvolden, JG Lawless, C. Ponnamperuma: Nonprotein Amino Acids in the Murchison Meteorite. In: Proceedings of the National Academy of Sciences. 68, 1971, p. 486, doi : 10.1073 / pnas.68.2.486 .
- ↑ Westerhoff, Ole (2002): Representation of unnatural α-amino acid derivatives by addition reactions to acyclic and cyclic imines. Dissertation, University of Oldenburg. urn : nbn: de: gbv: 715-oops-3390
- ↑ kup.at: Clarification of congenital metabolic diseases with the main symptom epilepsy , accessed on January 28, 2016.
- ↑ kindernetzwerk.de: Disease Overviews - Zellweger Syndrome , accessed on January 28, 2016.