α -Aminoadipic acid
Names | |
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IUPAC name
2-Aminohexanedioic acid
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Other names
2-Aminoadipic acid
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Identifiers | |
3D model (JSmol)
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1724349 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.009 |
EC Number |
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MeSH | 2-Aminoadipic+Acid |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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
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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).
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Metabolism[edit]
Lysine degradation[edit]
Through saccharopine and allysine, lysine is converted to
- allysine + NAD(P)+ ↔
α -aminoadipate NAD(P)H + H+
α -aminoadipate +α -ketoglutarate ↔α -ketoadipate + glutamate
Lysine biosynthesis[edit]
Importance[edit]
A 2013 study identified
D-
References[edit]
- ^ "2-Aminohexanedioic acid". pubchem.ncbi.nlm.nih.gov.
- ^ a b c Voet D, Voet JG (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-91745-9.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Xu H, Andi B, Qian J, West AH, Cook PF (2006). "The
α -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. - ^ 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.
- ^ 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.