Α-Aminoadipic acid pathway

α-Aminoadipic acid

Names
IUPAC name 2-aminohexanedioic acid
Identifiers
CAS Number	542-32-5 N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:37024 Y
ChemSpider	456 Y
MeSH	2-Aminoadipic+Acid
PubChem CID	469
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
Main hazards	Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

The α-aminoadipate pathway is a biochemical pathway for the synthesis of the amino acid L-lysine. In the eukaryotes, this pathway is unique to the higher fungi (containing chitin in their cell walls) and the euglenids. It has also been reported from bacteria of the genus Thermus.

Homocitrate is initially synthesised from acetyl-CoA and 2-oxoglutarate by homocitrate synthase. This is then converted to homoaconitate by homoaconitase and then to homoisocitrate by homoisocitrate dehydrogenase. A nitrogen atom is added from glutamate by aminoadipate aminotransferase to form the α-aminoadipate from which this pathway gets its name. This is then reduced by aminoadipate reductase via an acyl-enzyme intermediate to a semialdehyde. Reaction with glutamate by one class of saccharopine dehydrogenase yields saccharopine which is then cleaved by a second saccharopine dehydrogenase to yield lysine and oxoglutarate.

α-Aminoadipic acid is an intermediate in the α-Aminoadipic acid pathway for the metabolism of lysine and saccharopine. It is synthesised from homoisocitrate by aminoadipate aminotransferase and reduced by aminoadipate reductase to form the semialdehyde.