Dehydroalanine
From Wikipedia, the free encyclopedia
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Dehydroalanine |
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| Systematic (IUPAC) name | |
| 2-aminoprop-2-enoic acid | |
| Identifiers | |
| PubChem | 123991 |
| Chemical data | |
| Formula | C3H5NO2 |
| Molar mass | 87.077 |
| SMILES | C=C(C(=O)O)N |
| Complete data | |
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 protein, e.g., casein, that have been heated and/or treated with alkali (e;g., NaOH). These treatments can dehydrate serine in the protein chain. In food DHA frequently alkylates lysine to yield the crosslinking aminoacid lysinoalanine (LAL). LAL itself can be toxic, particularly to the kidney of rats.
Many dehydroalanine-containing peptides are toxic or antibiotic. They are a part of lantibiotics or microcystins.
