Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Αあるふぁ-Aminoadipic acid: Difference between pages

{{cs1 config|name-list-style=vanc}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477318813

| Name=αあるふぁ-Aminoadipic acid

| ImageFile=Alpha-aminoadipic acid.svg

| ImageSize=

| IUPACName=2-Aminohexanedioic acid

| OtherNames=2-Aminoadipic acid

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| Beilstein = 1724349

| EC_number = 208-809-2

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=542-32-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1K7B1OED4N

| PubChem=469

| ChEBI_Ref = {{ebicite|correct|EBI}}

| MeSHName=2-Aminoadipic+Acid

|Section2={{Chembox Properties

| Formula=C₆H₁₁NO₄

| MolarMass=161.156 g/mol

| Appearance=Crystalline

| Density=1.333 g/mL

| MeltingPtC=196

| BoilingPtC=364

| Solubility=

|Section3={{Chembox Hazards

| MainHazards=Irritant

| FlashPt=

| AutoignitionPt =

| 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あるふぁ-Aminoadipic acid''' is one of the [[Metabolism|metabolic]] precursor in the biosynthesis of [[lysine]] through [[Αあるふぁ-Aminoadipate pathway|αあるふぁ-aminoadipate pathway]]. Its [[conjugate base]] is '''αあるふぁ-aminoadipate''', which is the prevalent form at [[physiological pH]].

αあるふぁ-Aminoadipic acid has a [[stereogenic center]] and can appear in two [[Enantiomer|enantiomers]], <small>L</small>-αあるふぁ-aminoadipate and <small>D</small>-αあるふぁ-aminoadipate. The <small>L</small>-enantiomer appears during lysine biosynthesis and degradation, whereas the <small>D</small>-enantiomer is a part of certain [[antibiotics]].

== Metabolism ==

=== Lysine degradation ===

Through [[saccharopine]] and [[allysine]], lysine is converted to αあるふぁ-aminoadipate, which is then degraded all the way to [[acetoacetate]].<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 [[L-aminoadipate-semialdehyde dehydrogenase|aminoadipate-semialdehyde dehydrogenase]]:<ref name=":0" />

: allysine + NAD(P)⁺ ↔ αあるふぁ-aminoadipate NAD(P)H + H⁺

αあるふぁ-Aminoadipate is then transaminated with [[αあるふぁ-ketoglutarate]] to give [[2-ketoadipate|αあるふぁ-ketoadipate]] and [[glutamate]], respectively, by the action of [[2-aminoadipate transaminase]]:<ref name=":0" />

: αあるふぁ-aminoadipate + αあるふぁ-ketoglutarate ↔ αあるふぁ-ketoadipate + glutamate

=== Lysine biosynthesis ===

αあるふぁ-Aminoadipate appears during biosynthesis of lysine in several [[yeast]] species, [[fungi]], and certain [[Protist|protists]].<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=[[Cell Biochemistry and Biophysics]] |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, [[Αあるふぁ-Aminoadipate pathway|which is named after αあるふぁ-aminoadipate]], the same steps are repeated in the opposite order as in the degradation reactions, namely, αあるふぁ-ketoadipate is transaminated to αあるふぁ-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あるふぁ-aminoadipate pathway for lysine biosynthesis in fungi |journal=[[Cell Biochemistry and Biophysics]] |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あるふぁ-aminoadipate as a novel predictor of the development of [[diabetes]] and suggested that it is a potential modulator of [[glucose]] 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あるふぁ-Aminoadipic acid is a part of the antibiotic [[cephalosporin C]].<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あるふぁ-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あるふぁ-Aminoadipic acid}}

{{DEFAULTSORT:Aminoadipic acid}}

[[Category:Amino acids]]

[[Category:Dicarboxylic acids]]