Α-Aminoadipic acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
α-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).
Close

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]

2D representation of the chemical structure of Q28529674.
L-allysine
+ NAD+
 
 
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
+ 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]

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

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

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