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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
3D model (JSmol)
1724349
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.008.009Edit this at Wikidata
EC Number
  • 208-809-2
MeSH2-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 mass161.156 g/mol
AppearanceCrystalline
Density1.333 g/mL
Melting point196 °C (385 °F; 469 K)
Boiling point364 °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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

α-Aminoadipic acid is one of themetabolic precursor in the biosynthesis oflysine throughα-aminoadipate pathway. Itsconjugate base isα-aminoadipate, which is the prevalent form atphysiological pH.

α-Aminoadipic acid has astereogenic center and can appear in twoenantiomers,L-α-aminoadipate andD-α-aminoadipate. TheL-enantiomer appears during lysine biosynthesis and degradation, whereas theD-enantiomer is a part of certainantibiotics.

Metabolism

[edit]

Lysine degradation

[edit]

Throughsaccharopine and allysine, lysine is converted to α-aminoadipate, which is then degraded all the way toacetoacetate.[2] Allysine is oxidized byaminoadipate-semialdehyde dehydrogenase:[2]

2D representation of the chemical structure of Q28529674.
 
 
H2O
H+
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H2O
H+
 
2D representation of the chemical structure of Q27104392.
(S)-2-aminoadipic acid
 

α-Aminoadipate is then transaminated with α-ketoglutaric acid to give 2-oxooadipic acid and L-glutamic acid, respectively, by the action of2-aminoadipate transaminase:[2][3]

2D representation of the chemical structure of Q27104392.
+
 
2D representation of the chemical structure of α-Ketoglutaric acid .
 
 
 
Reversible left-right reaction arrow
 
 
 
2D representation of the chemical structure of 2-Oxoadipic acid .
+
 
2D representation of the chemical structure of Q26995161.

Lysine biosynthesis

[edit]

α-Aminoadipate appears during biosynthesis of lysine in severalyeast species,fungi, and certainprotists.[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

[edit]

A 2013 study identifieds α-aminoadipate as a novel predictor of the development ofdiabetes and suggested that it is a potential modulator ofglucose homeostasis in humans.[8]

D-α-Aminoadipic acid is a part of the antibioticcephalosporin C.[9]

References

[edit]
  1. ^"2-Aminohexanedioic acid".pubchem.ncbi.nlm.nih.gov.
  2. ^abcVoet D, Voet JG (2011).Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041.ISBN 978-0-470-91745-9.
  3. ^Enzyme2.6.1.34 atKEGG Pathway Database.
  4. ^abXu 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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