α-Aminoadipic acid is one of the metabolic precursor in the biosynthesis of lysine through α-aminoadipate pathway. Its conjugate base is α-aminoadipate, which is the prevalent form at physiological pH.
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| Names | |
|---|---|
| IUPAC name
2-Aminohexanedioic acid | |
| Other names
2-Aminoadipic acid | |
| Identifiers | |
3D model (JSmol) |
|
| 1724349 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.009 |
| EC Number |
|
| MeSH | 2-Aminoadipic+Acid |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C6H11NO4 | |
| Molar mass | 161.156 g/mol |
| Appearance | Crystalline |
| Density | 1.333 g/mL |
| Melting point | 196 °C (385 °F; 469 K) |
| Boiling point | 364 °C (687 °F; 637 K) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Irritant |
| GHS labelling:[1] | |
 | |
| Warning | |
| H317 | |
| P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
α-Aminoadipic acid has a stereogenic center and can appear in two enantiomers, L-α-aminoadipate and D-α-aminoadipate. The L-enantiomer appears during lysine biosynthesis and degradation, whereas the D-enantiomer is a part of certain antibiotics.
Metabolism
Lysine degradation
Through saccharopine and allysine, lysine is converted to α-aminoadipate, which is then degraded all the way to acetoacetate.[2] Allysine is oxidized by aminoadipate-semialdehyde dehydrogenase:[2]
- allysine + NAD(P)+ ↔ α-aminoadipate NAD(P)H + H+
α-Aminoadipate is then transaminated with α-ketoglutarate to give α-ketoadipate and glutamate, respectively, by the action of 2-aminoadipate transaminase:[2]
- α-aminoadipate + α-ketoglutarate ↔ α-ketoadipate + glutamate
Lysine biosynthesis
α-Aminoadipate appears during biosynthesis of lysine in several yeast species, fungi, and certain protists.[3][4][5][6] During this pathway, which is named after α-aminoadipate, the same steps are repeated in the opposite order as in the degradation reactions, namely, α-ketoadipate is transaminated to α-aminoadipate, which is then reduced to allysine, allysine couples with glutamate to give saccharopine, which is then cleaved to give lysine.[7]
Importance
A 2013 study identified α-aminoadipate as a novel predictor of the development of diabetes and suggested that it is a potential modulator of glucose homeostasis in humans.[8]
D-α-Aminoadipic acid is a part of the antibiotic cephalosporin C.[9]
References
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