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α-Aminoadipic acid

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α-Aminoadipic acid
Names
IUPAC name 2-Aminohexanedioic acid
Other names 2-Aminoadipic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1724349
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.009 Edit this at Wikidata
EC Number
  • 208-809-2
MeSH 2-Aminoadipic+Acid
PubChem CID
UNII
CompTox Dashboard (EPA)
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 GHS07: Exclamation mark
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. Allysine is oxidized by aminoadipate-semialdehyde dehydrogenase:

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:

α-aminoadipate + α-ketoglutarate ↔ α-ketoadipate + glutamate

Lysine biosynthesis

α-Aminoadipate appears during biosynthesis of lysine in several yeast species, fungi, and certain protists. 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.

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.

D-α-Aminoadipic acid is a part of the antibiotic cephalosporin C.

References

  1. "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.
  2. ^ Voet D, Voet JG (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-91745-9.
  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.
  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.
  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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