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Dehydroalanine

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Dehydroalanine
Structural formula
Ball-and-stick model of the zwitterion
Names
IUPAC name 2-Aminoprop-2-enoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)Key: UQBOJOOOTLPNST-UHFFFAOYSA-N
  • InChI=1/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6)Key: UQBOJOOOTLPNST-UHFFFAOYAW
SMILES
  • C=C(C(=O)O)N
  • O=C(O)C(=C)N
Properties
Chemical formula C3H5NO2
Molar mass 87.08 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).

Dehydroalanine (DHA) is also found in food proteins, including casein, that have been heated and/or treated with an alkali such as sodium hydroxide (NaOH). These treatments can dehydrate serine in the protein chain. In food, DHA frequently alkylates lysine to yield the crosslinking aminoacid lysinoalanine (LAL). Lysinoalanine, N6-(DL-2-amino-2-carboxyethyl)-L-lysine, an unusual amino acid implicated as a renal toxic factor in laboratory rats (kidney damage), has been found in proteins of home-cooked and commercial foods and ingredients. Although it had been reported to occur in both edible and non-food proteins only after alkali treatment (such as occurs in soybean processing), it has also been identified in food proteins that had not been subjected to alkali. Lysinoalanine can also be generated in a variety of proteins when heated under non-alkaline conditions.

Many dehydroalanine-containing peptides are toxic or antibiotic and constitute parts of lantibiotics or microcystins.

See also

References

CID 123991 from PubChem

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