Α-Aminoadipic acid

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Contents

α-Aminoadipic acid
Alpha-aminoadipic acid.svg
Names
IUPAC name
2-Aminohexanedioic acid
Other names
2-Aminoadipic acid
Identifiers
3D model (JSmol)
1724349
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.009 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-809-2
MeSH 2-Aminoadipic+Acid
PubChem CID
UNII
  • InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) Yes check.svgY
    Key: OYIFNHCXNCRBQI-UHFFFAOYSA-N Yes check.svgY
  • 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
  • C(CC(C(=O)O)N)CC(=O)O
  • O=C(O)CCCC(N)C(=O)O
Properties
C6H11NO4
Molar mass 161.156 g/mol
AppearanceCrystalline
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]
GHS-pictogram-exclam.svg
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 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]

L-allysine.svg
L-allysine
+ NAD+
 
 
H2O
H+
A-Aminoadipic acid
H2O
H+
 
L-2-aminoadipic acid.svg
(S)-2-aminoadipic acid
+ NADH
 

α-Aminoadipate is then transaminated with α-ketoglutaric acid to give 2-oxooadipic acid and L-glutamic acid, respectively, by the action of 2-aminoadipate transaminase: [2] [3]

Lysine biosynthesis

α-Aminoadipate appears during biosynthesis of lysine in several yeast species, fungi, and certain protists. [4] [5] [6] [7] 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. [4]

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]

References

  1. ↑ "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.
  2. 1 2 3 Voet D, Voet JG (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN   978-0-470-91745-9.
  3. ↑ Enzyme 2.6.1.34 at KEGG Pathway Database.
  4. 1 2 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  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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