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α-Aminoadipate pathway

The α-aminoadipate pathway is a biochemical pathway for the synthesis of the amino acid L-lysine. In the eukaryotes, this pathway is unique to the higher fungi (containing chitin in their cell walls) and the euglenids.[1] It has also been reported from bacteria of the genus Thermus.[2]

The amino acid L-lysine

Pathway overview Edit

Homocitrate is initially synthesised from acetyl-CoA and 2-oxoglutarate by homocitrate synthase. This is then converted to homoaconitate by homoaconitase and then to homoisocitrate by homoisocitrate dehydrogenase. A nitrogen atom is added from glutamate by aminoadipate aminotransferase to form the α-aminoadipate from which this pathway gets its name. This is then reduced by aminoadipate reductase via an acyl-enzyme intermediate to a semialdehyde. Reaction with glutamate by one class of saccharopine dehydrogenase yields saccharopine which is then cleaved by a second saccharopine dehydrogenase to yield lysine and oxoglutarate.[3]

α-Aminoadipic acid Edit

α-Aminoadipic acid
 
Names
IUPAC name
2-Aminohexanedioic acid
Other names
2-Aminoadipic acid
Identifiers
  • 542-32-5  Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:37024  Y
ChEMBL
  • ChEMBL433238  Y
ChemSpider
  • 456  Y
MeSH 2-Aminoadipic+Acid
  • 469
UNII
  • 1K7B1OED4N  Y
  • InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)  Y
    Key: OYIFNHCXNCRBQI-UHFFFAOYSA-N  Y
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what is  Y N ?)

α-Aminoadipic acid is the conjugate acid of α-aminoadipate, the latter of which is the prevalent form at physiological pH. A 2013 study identified α-Aminoadipic acid (2-aminoadipic acid) as a novel predictor of the development of diabetes and suggested that it is a potential modulator of glucose homeostasis in humans.[4]

See also Edit

References Edit

  1. ^ Zabriskie TM, Jackson MD (2000). "Lysine biosynthesis and metabolism in fungi". Natural Product Reports. 17 (1): 85–97. doi:10.1039/a801345d. PMID 10714900.
  2. ^ Kosuge T, Hoshino T (1999). "The α-aminoadipate pathway for lysine biosynthesis is widely distributed among Thermus strains". Journal of Bioscience and Bioengineering. 88 (6): 672–5. doi:10.1016/S1389-1723(00)87099-1. PMID 16232683.
  3. ^ 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.
  4. ^ 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.


aminoadipate, pathway, been, suggested, that, this, article, should, split, into, articles, titled, aminoadipic, acid, discuss, february, 2022, aminoadipate, pathway, biochemical, pathway, synthesis, amino, acid, lysine, eukaryotes, this, pathway, unique, high. It has been suggested that this article should be split into articles titled a Aminoadipate pathway and a Aminoadipic acid discuss February 2022 The a aminoadipate pathway is a biochemical pathway for the synthesis of the amino acid L lysine In the eukaryotes this pathway is unique to the higher fungi containing chitin in their cell walls and the euglenids 1 It has also been reported from bacteria of the genus Thermus 2 The amino acid L lysine Contents 1 Pathway overview 2 a Aminoadipic acid 3 See also 4 ReferencesPathway overview EditHomocitrate is initially synthesised from acetyl CoA and 2 oxoglutarate by homocitrate synthase This is then converted to homoaconitate by homoaconitase and then to homoisocitrate by homoisocitrate dehydrogenase A nitrogen atom is added from glutamate by aminoadipate aminotransferase to form the a aminoadipate from which this pathway gets its name This is then reduced by aminoadipate reductase via an acyl enzyme intermediate to a semialdehyde Reaction with glutamate by one class of saccharopine dehydrogenase yields saccharopine which is then cleaved by a second saccharopine dehydrogenase to yield lysine and oxoglutarate 3 a Aminoadipic acid Edita Aminoadipic acid NamesIUPAC name 2 Aminohexanedioic acidOther names 2 Aminoadipic acidIdentifiersCAS Number 542 32 5 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 37024 YChEMBL ChEMBL433238 YChemSpider 456 YMeSH 2 Aminoadipic AcidPubChem CID 469UNII 1K7B1OED4N YInChI InChI 1S C6H11NO4 c7 4 6 10 11 2 1 3 5 8 9 h4H 1 3 7H2 H 8 9 H 10 11 YKey OYIFNHCXNCRBQI UHFFFAOYSA N YInChI 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 UHFFFAOYACSMILES C CC C O O N CC O OO C O CCCC N C O OPropertiesChemical formula C6H11NO4Molar mass 161 156 g molAppearance CrystallineDensity 1 333 g mLMelting point 196 C 385 F 469 K Boiling point 364 C 687 F 637 K HazardsOccupational safety and health OHS OSH Main hazards IrritantExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references a Aminoadipic acid is the conjugate acid of a aminoadipate the latter of which is the prevalent form at physiological pH A 2013 study identified a Aminoadipic acid 2 aminoadipic acid as a novel predictor of the development of diabetes and suggested that it is a potential modulator of glucose homeostasis in humans 4 See also EditAdipic acidReferences Edit Zabriskie TM Jackson MD 2000 Lysine biosynthesis and metabolism in fungi Natural Product Reports 17 1 85 97 doi 10 1039 a801345d PMID 10714900 Kosuge T Hoshino T 1999 The a aminoadipate pathway for lysine biosynthesis is widely distributed among Thermus strains Journal of Bioscience and Bioengineering 88 6 672 5 doi 10 1016 S1389 1723 00 87099 1 PMID 16232683 Xu H Andi B Qian J West AH Cook PF 2006 The a 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 This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title A Aminoadipate pathway amp oldid 1160802555, wikipedia, wiki, book, books, library,

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