Oxalyldiaminopropionic acid

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Structural formula
Structural formula of oxalyldiaminopropionic acid
General
Surname Oxalyldiaminopropionic acid
other names
  • 3 - [(carboxycarbonyl) amino] - L -alanine
  • β-oxalylamino- L- alanine; BOAA
  • β- N -oxalyl- L -α, β-diaminopropionic acid; ODAP
  • L-Dencichin
Molecular formula C 5 H 8 N 2 O 5
External identifiers / databases
CAS number 5302-45-4
PubChem 440259
ChemSpider 389238
Wikidata Q409824
properties
Molar mass 176.13 g mol −1
Physical state

firmly

Melting point

206 ° C (disintegration of the monohydrate)

pK s value

1.95
2.95
9.25

safety instructions
GHS hazard labeling
no classification available
Toxicological data

301 mg kg −1 ( LD 50 ,  mouse ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxalyldiaminopropionic acid is a non-proteinogenic amino acid found in the common pea ( Lathyrus sativus ). The substance is neurotoxic and is believed to cause lathyrism . It leads to cramps and spastic paralysis . This is probably a consequence of the similarity with L -glutamate .

biosynthesis

Oxalyldiaminopropionic acid is synthesized in the plant from L- asparagine .

Crystallization

A metastable monohydrate and a stable anhydrate exist as crystal forms .

Individual evidence

  1. ↑ Haskell, BE; Bowlus, SB: in J. Org. Chem. 41 : 159-160 (1976).
  2. ↑ a b c d Paul O'Brien, Peter B. Nunn: Dimorphism of β-n-oxalyl-l- α, β- diaminopropionic acid . In: Phytochemistry . tape 21 , no. January 8 , 1982, ISSN  0031-9422 , pp. 2001-2004 , doi : 10.1016 / 0031-9422 (82) 83031-8 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ Entry on oxalyldiaminopropionic acid in the ChemIDplus database of the United States National Library of Medicine (NLM)
  5. ↑ BA Warren, SA Patel, PB Nunn, RJ Bridges: The Lathyrus excitotoxin β-N-oxalyl-l- α, β- diaminopropionic acid is a substrate of the L-cystine / L-glutamate exchanger system x c - . In: Toxicology and Applied Pharmacology . tape 200 , no. 2 , 2004, p. 83-92 , doi : 10.1016 / j.taap.2004.04.001 .
  6. ^ PM Dey, JB Harborne, Plant Biochemistry . Elsevier, 1997. ISBN 978-0-12-214674-9 . P. 442.