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| Names | |
|---|---|
| Preferred IUPAC name (2S)-2-Amino-6-oxohexanoic acid | |
| Other names 2-aminoadipate semialdehyde, 2-amino-5-formylvaleric acid, norvaline, 6-oxo-DL-norleucine | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| KEGG |
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| MeSH | allysine |
| UNII | |
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| Properties | |
| C6H11NO3 | |
| Molar mass | 145.158 g·mol−1 |
| Appearance | unstable |
| Density | 1.74g/cm3 |
| Boiling point | 295.2 °C (563.4 °F; 568.3 K) |
| Hazards | |
| Flash point | 132.3 °C (270.1 °F; 405.4 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Allysine is a derivative oflysine that features a formyl group in place of the terminal amine. The free amino acid does not exist, but the allysineresidue does. It is produced by aerobic oxidation of lysine residues by the enzymelysyl oxidase. The transformation is an example of apost-translational modification. Thesemialdehyde form exists in equilibrium with a cyclic derivative.[1]
Allysine is linked to L-lysine in reactions catalysed bysaccharopine dehydrogenases. These interconvert them via saccharopine:[2][3][4]
Allysine is involved in the production ofelastin andcollagen.[5] Increased allysine concentration in tissues has been correlated to the presence of fibrosis.[6]
Allysine residues react with sodium 2-naphthol-6-sulfonate to produce afluorescent bis-naphtol-allysine product.[7] In another assay, allysine-containing proteins are reduced with sodium borohydride to give a peptide containing the 6-hydroxynorleucine (6-hydroxy-2-aminocaproic acid) residue, which (unlike allysine) is stable to proteolysis.[1]
