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α-Aminoadipic acid - Wikipedia
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αあるふぁ-Aminoadipic acid

(Redirected from Alpha-Aminoadipic acid)

αあるふぁ-Aminoadipic acid is one of the metabolic precursor in the biosynthesis of lysine through αあるふぁ-aminoadipate pathway. Its conjugate base is αあるふぁ-aminoadipate, which is the prevalent form at physiological pH.

αあるふぁ-Aminoadipic acid
Names
IUPAC name
2-Aminohexanedioic acid
Other names
2-Aminoadipic acid
Identifiers
3D model (JSmol)
1724349
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.009 Edit this at Wikidata
EC Number
  • 208-809-2
MeSH 2-Aminoadipic+Acid
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) checkY
    Key: OYIFNHCXNCRBQI-UHFFFAOYSA-N checkY
  • 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
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]
GHS07: Exclamation mark
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).
☒N verify (what is checkY☒N ?)

αあるふぁ-Aminoadipic acid has a stereogenic center and can appear in two enantiomers, L-αあるふぁ-aminoadipate and D-αあるふぁ-aminoadipate. The L-enantiomer appears during lysine biosynthesis and degradation, whereas the D-enantiomer is a part of certain antibiotics.

Metabolism edit

Lysine degradation edit

Through saccharopine and allysine, lysine is converted to αあるふぁ-aminoadipate, which is then degraded all the way to acetoacetate.[2] Allysine is oxidized by aminoadipate-semialdehyde dehydrogenase:[2]

allysine + NAD(P)+ ↔ αあるふぁ-aminoadipate NAD(P)H + H+

αあるふぁ-Aminoadipate is then transaminated with αあるふぁ-ketoglutarate to give αあるふぁ-ketoadipate and glutamate, respectively, by the action of 2-aminoadipate transaminase:[2]

αあるふぁ-aminoadipate + αあるふぁ-ketoglutarate ↔ αあるふぁ-ketoadipate + glutamate

Lysine biosynthesis edit

αあるふぁ-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あるふぁ-aminoadipate, the same steps are repeated in the opposite order as in the degradation reactions, namely, αあるふぁ-ketoadipate is transaminated to αあるふぁ-aminoadipate, which is then reduced to allysine, allysine couples with glutamate to give saccharopine, which is then cleaved to give lysine.[7]

Importance edit

A 2013 study identified αあるふぁ-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あるふぁ-Aminoadipic acid is a part of the antibiotic cephalosporin C.[9]

References edit

  1. ^ "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.
  2. ^ a b c 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あるふぁ-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あるふぁ-Aminoadipic Acid". Nature. 175 (4456): 548. Bibcode:1955Natur.175..548N. doi:10.1038/175548a0. ISSN 1476-4687. PMID 14370161.
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