α-Aminoadipic acid

α-Aminoadipic acid
Names
	IUPAC name 2-Aminohexanedioic acid
	Other names 2-Aminoadipic acid
Identifiers
CAS Number	542-32-5 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1724349
ChEBI	CHEBI:37024 ;
ChEMBL	ChEMBL433238 ;
ChemSpider	456 ;
ECHA InfoCard	100.008.009
EC Number	208-809-2;
MeSH	2-Aminoadipic+Acid
PubChem CID	469;
UNII	1K7B1OED4N ;
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) Key: OYIFNHCXNCRBQI-UHFFFAOYSA-N ; 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:
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). verify (what is ?) Infobox references

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 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

^ "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b ^c Voet D, Voet JG (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-91745-9.
^ Xu H, Andi B, Qian J, West AH, Cook PF (2006). "The alpha-aminoadipate pathway for lysine biosynthesis in fungi". Cell Biochemistry and Biophysics. 46 (1): 43–64. doi:10.1385/CBB:46:1:43. PMID 16943623. S2CID 22370361.
^ Andi B, West AH, Cook PF (September 2004). "Kinetic mechanism of histidine-tagged homocitrate synthase from Saccharomyces cerevisiae". Biochemistry. 43 (37): 11790–11795. doi:10.1021/bi048766p. PMID 15362863.
^ Bhattacharjee JK (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes". Critical Reviews in Microbiology. 12 (2): 131–151. doi:10.3109/10408418509104427. PMID 3928261.
^ Bhattacharjee JK, Strassman M (May 1967). "Accumulation of tricarboxylic acids related to lysine biosynthesis in a yeast mutant". The Journal of Biological Chemistry. 242 (10): 2542–2546. doi:10.1016/S0021-9258(18)95997-1. PMID 6026248.
^ Xu H, Andi B, Qian J, West AH, Cook PF (2006). "The α-aminoadipate pathway for lysine biosynthesis in fungi". Cell Biochemistry and Biophysics. 46 (1): 43–64. doi:10.1385/CBB:46:1:43. PMID 16943623. S2CID 22370361.
^ Wang TJ, Ngo D, Psychogios N, Dejam A, Larson MG, Vasan RS, Ghorbani A, O'Sullivan J, Cheng S, Rhee EP, Sinha S, McCabe E, Fox CS, O'Donnell CJ, Ho JE, Florez JC, Magnusson M, Pierce KA, Souza AL, Yu Y, Carter C, Light PE, Melander O, Clish CB, Gerszten RE (2013). "2-Aminoadipic acid is a biomarker for diabetes risk". Journal of Clinical Investigation. 123 (10): 4309–4317. doi:10.1172/JCI64801. PMC 3784523. PMID 24091325.
^ Newton GG, Abraham EP (1955). "Cephalosporin C, a New Antibiotic containing Sulphur and D-α-Aminoadipic Acid". Nature. 175 (4456): 548. Bibcode:1955Natur.175..548N. doi:10.1038/175548a0. ISSN 1476-4687. PMID 14370161.

[1] "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.

[:0-2] Voet D, Voet JG (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-91745-9.

[Xu_2006-3] Xu H, Andi B, Qian J, West AH, Cook PF (2006). "The alpha-aminoadipate pathway for lysine biosynthesis in fungi". Cell Biochemistry and Biophysics. 46 (1): 43–64. doi:10.1385/CBB:46:1:43. PMID 16943623. S2CID 22370361.

[4] Andi B, West AH, Cook PF (September 2004). "Kinetic mechanism of histidine-tagged homocitrate synthase from Saccharomyces cerevisiae". Biochemistry. 43 (37): 11790–11795. doi:10.1021/bi048766p. PMID 15362863.

[5] Bhattacharjee JK (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes". Critical Reviews in Microbiology. 12 (2): 131–151. doi:10.3109/10408418509104427. PMID 3928261.

[6] Bhattacharjee JK, Strassman M (May 1967). "Accumulation of tricarboxylic acids related to lysine biosynthesis in a yeast mutant". The Journal of Biological Chemistry. 242 (10): 2542–2546. doi:10.1016/S0021-9258(18)95997-1. PMID 6026248.

[pmid16943623-7] Xu H, Andi B, Qian J, West AH, Cook PF (2006). "The α-aminoadipate pathway for lysine biosynthesis in fungi". Cell Biochemistry and Biophysics. 46 (1): 43–64. doi:10.1385/CBB:46:1:43. PMID 16943623. S2CID 22370361.

[Wang-8] Wang TJ, Ngo D, Psychogios N, Dejam A, Larson MG, Vasan RS, Ghorbani A, O'Sullivan J, Cheng S, Rhee EP, Sinha S, McCabe E, Fox CS, O'Donnell CJ, Ho JE, Florez JC, Magnusson M, Pierce KA, Souza AL, Yu Y, Carter C, Light PE, Melander O, Clish CB, Gerszten RE (2013). "2-Aminoadipic acid is a biomarker for diabetes risk". Journal of Clinical Investigation. 123 (10): 4309–4317. doi:10.1172/JCI64801. PMC 3784523. PMID 24091325.

[9] Newton GG, Abraham EP (1955). "Cephalosporin C, a New Antibiotic containing Sulphur and D-α-Aminoadipic Acid". Nature. 175 (4456): 548. Bibcode:1955Natur.175..548N. doi:10.1038/175548a0. ISSN 1476-4687. PMID 14370161.

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