Dehydroalanine

Dehydroalanine
IUPAC name 2-Aminoprop-2-enoic acid
Identifiers
CAS number	1948-56-7
PubChem	123991
ChemSpider	110510 Y
DrugBank	DB02688
KEGG	C02218 Y
ChEBI	CHEBI:17123 Y
Jmol-3D images	Image 1 Image 2
SMILES C=C(C(=O)O)N O=C(O)C(=C)N
InChI InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) Y Key: UQBOJOOOTLPNST-UHFFFAOYSA-N Y InChI=1/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) Key: UQBOJOOOTLPNST-UHFFFAOYAW
Properties
Molecular formula	C3H5NO2
Molar mass	87.08 g/mol
Density	1.222 g/mL
Boiling point	251.2 °C; 484.2 °F; 524.3 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

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

• Lanthionine

References

PubChem 123991