Α-Aminoadipic acid

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.

α-Aminoadipic acid

Names
IUPAC name 2-Aminohexanedioic acid
Other names 2-Aminoadipic acid
Identifiers
CAS Number	542-32-5 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1724349
ChEBI	CHEBI:37024 Y
ChEMBL	ChEMBL433238 Y
ChemSpider	456 Y
ECHA InfoCard	100.008.009
EC Number	208-809-2
MeSH	2-Aminoadipic+Acid
PubChem CID	469
UNII	1K7B1OED4N Y
CompTox Dashboard (EPA)	DTXSID90862154
InChI InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) Y Key: OYIFNHCXNCRBQI-UHFFFAOYSA-N Y InChI=1/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) Key: OYIFNHCXNCRBQI-UHFFFAOYAC
SMILES C(CC(C(=O)O)N)CC(=O)O O=C(O)CCCC(N)C(=O)O
Properties
Chemical formula	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]
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	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). N verify (what is YN ?) Infobox references

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 identifieds 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]