![]() | |
Names | |
---|---|
IUPAC name
2-Aminohexanedioic acid
| |
Other names
2-Aminoadipic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
1724349 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.009 |
EC Number |
|
MeSH | 2-Aminoadipic+Acid |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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] | |
![]() | |
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.
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]
α-Aminoadipate is then transaminated with α-ketoglutarate to give α-ketoadipate and glutamate, respectively, by the action of 2-aminoadipate transaminase: [2]
α-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-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. [7]
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. [8]
D-α-Aminoadipic acid is a part of the antibiotic cephalosporin C. [9]
![]() | |
Names | |
---|---|
IUPAC name
2-Aminohexanedioic acid
| |
Other names
2-Aminoadipic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
1724349 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.009 |
EC Number |
|
MeSH | 2-Aminoadipic+Acid |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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] | |
![]() | |
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.
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]
α-Aminoadipate is then transaminated with α-ketoglutarate to give α-ketoadipate and glutamate, respectively, by the action of 2-aminoadipate transaminase: [2]
α-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-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. [7]
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. [8]
D-α-Aminoadipic acid is a part of the antibiotic cephalosporin C. [9]