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Revision as of 05:27, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 443379120 of page Alpha-Aminoadipic_acid for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 23:06, 6 March 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,058 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Removed proxy/dead URL that duplicated identifier. | Use this tool. Report bugs. | #UCB_Gadget 
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{{cs1 config|name-list-style=vanc}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443377661
| Watchedfields = changed
⚫ |Name=α-Aminoadipic acid
⚫ | verifiedrevid = 477318813
⚫ |ImageFile=Alpha-aminoadipic acid.svg
⚫ | Name=α-Aminoadipic acid
⚫ |ImageSize=
⚫ | ImageFile=Alpha-aminoadipic acid.svg
⚫ |IUPACName=2-aminohexanedioic acid
⚫ | ImageSize=
|OtherNames=
⚫ | IUPACName=2-Aminohexanedioic acid
⚫ |Section1= {{Chembox Identifiers
| OtherNames=2-Aminoadipic acid
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 456 | ChemSpiderID = 456
| SMILES1 = O=C(O)CCCC(N)C(=O)O | SMILES1 = O=C(O)CCCC(N)C(=O)O
| InChI = 1/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) | InChI = 1/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)
| InChIKey = OYIFNHCXNCRBQI-UHFFFAOYAC | InChIKey = OYIFNHCXNCRBQI-UHFFFAOYAC
| Beilstein = 1724349
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 433238 | ChEMBL = 433238
| EC_number = 208-809-2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) | StdInChI = 1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OYIFNHCXNCRBQI-UHFFFAOYSA-N | StdInChIKey = OYIFNHCXNCRBQI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 542-32-5 -->
| CASNo=542-32-5
⚫ | PubChem=469
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1K7B1OED4N
⚫ | PubChem=469
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 37024 | ChEBI = 37024
| SMILES=C(CC(C(=O)O)N)CC(=O)O | SMILES=C(CC(C(=O)O)N)CC(=O)O
| MeSHName=2-Aminoadipic+Acid | MeSHName=2-Aminoadipic+Acid
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>6</sub>H<sub>11</sub>NO<sub>4</sub> | Formula=C<sub>6</sub>H<sub>11</sub>NO<sub>4</sub>
| MolarMass=161.156 g/mol | MolarMass=161.156 g/mol
| Appearance= | Appearance=Crystalline
| Density= | Density=1.333 g/mL
| MeltingPtC=196
| MeltingPt=
| BoilingPtC=364
| BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=Irritant
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
| GHS_ref=<ref>{{cite web |title=2-Aminohexanedioic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/469#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|317}}
| PPhrases = {{P-phrases|261|272|280|302+352|321|333+317|362+364|501}}
}} }}
}} }}

'''α-Aminoadipic acid''' is one of the ] precursor in the biosynthesis of ] through ]. Its ] is '''α-aminoadipate''', which is the prevalent form at ].

α-Aminoadipic acid has a ] and can appear in two ], <small>L</small>-α-aminoadipate and <small>D</small>-α-aminoadipate. The <small>L</small>-enantiomer appears during lysine biosynthesis and degradation, whereas the <small>D</small>-enantiomer is a part of certain ].

== Metabolism ==

=== Lysine degradation ===
Through ] and ], lysine is converted to α-aminoadipate, which is then degraded all the way to ].<ref name=":0">{{Cite book |last1=Voet |first1=Donald |title=Biochemistry |last2=Voet |first2=Judith G. |date=2011 |publisher=Wiley |isbn=978-0-470-91745-9 |edition=4th |location=Hoboken, NJ |pages=1040{{--}}1041}}</ref> Allysine is oxidized by ]:<ref name=":0" />

: allysine + NAD(P)<sup>+</sup> ↔ α-aminoadipate NAD(P)H + H<sup>+</sup>

α-Aminoadipate is then transaminated with ] to give ] and ], respectively, by the action of ]:<ref name=":0" />

: α-aminoadipate + α-ketoglutarate ↔ α-ketoadipate + glutamate

=== Lysine biosynthesis ===
α-Aminoadipate appears during biosynthesis of lysine in several ] species, ], and certain ].<ref name="Xu_2006">{{cite journal |vauthors=Xu H, Andi B, Qian J, West AH, Cook PF |date=2006 |title=The alpha-aminoadipate pathway for lysine biosynthesis in fungi |journal=] |volume=46 |issue=1 |pages=43–64 |doi=10.1385/CBB:46:1:43 |pmid=16943623 |s2cid=22370361}}</ref><ref>{{cite journal |vauthors=Andi B, West AH, Cook PF |date=September 2004 |title=Kinetic mechanism of histidine-tagged homocitrate synthase from Saccharomyces cerevisiae |journal=Biochemistry |volume=43 |issue=37 |pages=11790–11795 |doi=10.1021/bi048766p |pmid=15362863}}</ref><ref>{{cite journal |vauthors=Bhattacharjee JK |date=1985 |title=alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes |journal=Critical Reviews in Microbiology |volume=12 |issue=2 |pages=131–151 |doi=10.3109/10408418509104427 |pmid=3928261}}</ref><ref>{{cite journal |vauthors=Bhattacharjee JK, Strassman M |date=May 1967 |title=Accumulation of tricarboxylic acids related to lysine biosynthesis in a yeast mutant |journal=The Journal of Biological Chemistry |volume=242 |issue=10 |pages=2542–2546 |doi=10.1016/S0021-9258(18)95997-1 |pmid=6026248 |doi-access=free}}</ref> During this pathway, ], 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.<ref name="pmid16943623">{{cite journal |vauthors=Xu H, Andi B, Qian J, West AH, Cook PF |year=2006 |title=The α-aminoadipate pathway for lysine biosynthesis in fungi |journal=] |volume=46 |issue=1 |pages=43–64 |doi=10.1385/CBB:46:1:43 |pmid=16943623 |s2cid=22370361}}</ref>

== Importance ==
A 2013 study identified α-aminoadipate as a novel predictor of the development of ] and suggested that it is a potential modulator of ] homeostasis in humans.<ref name="Wang">{{cite journal |title=2-Aminoadipic acid is a biomarker for diabetes risk |vauthors =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
|journal= Journal of Clinical Investigation|volume=123
|issue=10
|pages=4309–4317
|year=2013 |pmid= 24091325|doi=10.1172/JCI64801 |pmc=3784523}}</ref>

<small>D</small>-α-Aminoadipic acid is a part of the antibiotic ].<ref>{{Cite journal |last1=Newton |first1=G. G. F. |last2=Abraham |first2=E. P. |date=1955 |title=Cephalosporin C, a New Antibiotic containing Sulphur and D-α-Aminoadipic Acid |journal=Nature |language=en |volume=175 |issue=4456 |pages=548 |doi=10.1038/175548a0 |pmid=14370161 |bibcode=1955Natur.175..548N |issn=1476-4687|doi-access=free }}</ref>

== References ==
{{Reflist}}

{{DISPLAYTITLE:α-Aminoadipic acid}}
{{DEFAULTSORT:Aminoadipic acid}}
]
]
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