{{위키데이터 속성 추적}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 477319228
| Name = 알파-케토아이소카프로산<br>α-Ketoisocaproic acid
| ImageFile = Alpha-ketoisocaproic acid.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 244
| ImageName = Skeletal formula of ''alpha''-ketoisocaproic acid
| IUPACName = 4-Methyl-2-oxopentanoic acid
| SystematicName = 4-Methyl-2-oxopentanoic acid<ref>{{PubChem|70}}</ref>
| OtherNames = 4-Methyl-2-oxovaleric acid
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 4656
| CASNo = 816-66-0
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4GUJ8AH400
| PubChem = 70
| ChemSpiderID = 69
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 212-435-5
| UNNumber = 3265
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03229
| KEGG = C00233
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Alpha-ketoisocaproic+acid
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48430
| ChEMBL = 445647
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| Beilstein = 1701823
| 3DMet = B00066
| SMILES = CC(C)CC(=O)C(O)=O
| SMILES1 = O=C(C(=O)O)CC(C)C
| StdInChI = 1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)
| StdInChIKey = BKAJNAXTPSGJCU-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = BKAJNAXTPSGJCU-UHFFFAOYAG
}}
|Section2={{Chembox Properties
| C = 6
| H = 10
| O = 3
| Density = 1.055 g cm<sup>−3</sup> (at 20&nbsp;°C)
| MeltingPtC = 8 to 10
| BoilingPtC = 85
| BoilingPt_notes = at 13 mmHg
| LogP = 0.133
| pKa = 2.651
| pKb = 11.346
}}
|Section3={{Chembox Hazards
| EUClass = {{Hazchem C}}
| RPhrases = {{R34}}
| SPhrases = {{S26}}, {{S36/37/39}}, {{S45}}
}}
}}
'''α-케토아이소카프로산'''({{llang|en|α-ketoisocaproic acid}}) 또는 '''4-메틸-2-옥소펜탄산'''({{llang|en|4-methyl-2-oxopentanoic acid}})<ref>{{PubChem|70}}</ref>은 [[류신]]의 대사 과정에서의 [[대사 중간생성물]]이다.

==류신의 대사 경로==
{|
|[[파일:HMB biosynthesis and metabolism.png|섬네일|600px|왼쪽|사람에서 [[류신|L-류신]]과 관련한 [[β-하이드록시 β-메틸뷰티르산]](HMB) 및 [[아이소발레릴-CoA]]에 대한 [[대사 경로]]. 두 가지 주요 경로 중 L-류신은 대부분 아이소발레릴-CoA로 대사되는 반면, β-하이드록시 β-메틸뷰티르산(HMB)으로 대사되는 경우는 약 5%에 불과하다.<ref>{{저널 인용| vauthors = Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J | title = International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB) | journal = Journal of the International Society of Sports Nutrition | volume = 10 | issue = 1 | pages = 6 | date = February 2013 | pmid = 23374455 | pmc = 3568064 | doi = 10.1186/1550-2783-10-6}}</ref><ref>{{저널 인용| vauthors = Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH | title = HMB supplementation: clinical and athletic performance-related effects and mechanisms of action | journal = Amino Acids | volume = 40 | issue = 4 | pages = 1015–1025 | date = April 2011 | pmid = 20607321 | doi = 10.1007/s00726-010-0678-0 | quote = HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).<!--<br /><br /> In the second pathway, after transamination, [α-KIC] in liver generates isovaleryl-CoA through the enzymatic action of branched-chain ketoacid dehydrogenase (BCKD) and after several steps, there is production of HMG-CoA through the enzyme HMG-CoA synthase (Fig. 1). Under normal conditions the majority of KIC is converted into isovaleryl-CoA, in which approximately 5% of leucine is metabolized into HMB (Wilson et al. 2008; Van Koverin and Nissen 1992). However, Nissen and Abumrad (1997) provided evidence that the primary fate of HMB is probably conversion to HMG-CoA in the liver, for cholesterol biosynthesis.--> }}</ref><ref>{{서적 인용| vauthors=Kohlmeier M | title=Nutrient Metabolism: Structures, Functions, and Genes | date=May 2015 | publisher=Academic Press | isbn=978-0-12-387784-0 | pages=385–388 | edition=2nd | section-url=https://books.google.com/books?id=aTQTAAAAQBAJ&pg=PA387&q=beta-hydroxy%20beta-methylbutyrate%20HMB#v=onepage | url=https://books.google.com/books?id=aTQTAAAAQBAJ&printsec=frontcover#v=onepage | accessdate=6 June 2016 | section=Leucine | quote= Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours&nbsp;... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds}}<br />[https://books.google.com/books?id=aTQTAAAAQBAJ&pg=PA386#v=onepage&q&f=false Figure 8.57: Metabolism of {{smallcaps all|L}}-leucine]</ref>]]
|}

== 각주 ==
{{각주}}

{{아미노산 대사 중간생성물들}}

[[분류:알파-케토산]]