2-하이드록시아이소뷰티르산

2-하이드록시아이소뷰티르산
이름
	별칭 α-hydroxyisobutyric acid,; 2-hydroxyisobutanoic acid,; α-hydroxyisobutanoic acid,; 2-hydroxy-2-methyl propanoic acid,; 2-hydroxy-2-methyl propionic acid,; 2-methyllactic acid,; 2-methylglycolic acid,; acetonic acid,; hydroxydimethylacetic acid
식별자
CAS 번호	594-61-6 ;
3D 모델 (JSmol)	Interactive image;
바일슈타인; 레퍼런스	1744739
ChEBI	CHEBI:50129;
ChEMBL	ChEMBL1345148;
ChemSpider	11181;
ECHA InfoCard	100.008.955
EC 번호	209-848-8;
PubChem CID	11671;
UNII	DMW250U2HF;
CompTox Dashboard (EPA)	DTXSID4032954 ;
	InChI InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6) Key: BWLBGMIXKSTLSX-UHFFFAOYSA-N;
	SMILES CC(C)(C(=O)O)O;
성질
화학식	C4H8O3
몰 질량	104.105 g·mol−1
겉보기	흰색 고체
밀도	1.23 g/cm3
녹는점	82.5 °C (180.5 °F; 355.6 K)
끓는점	212 °C (414 °F; 485 K)
	달리 명시된 경우를 제외하면, 표준상태(25 °C [77 °F], 100 kPa)에서 물질의 정보가 제공됨. 정보상자 각주

2-하이드록시아이소뷰티르산(영어: 2-hydroxyisobutyric acid)은 화학식이 (CH
3)
2C(OH)CO
2H인 유기 화합물이다. 2-하이드록시아이소뷰티르산은 흰색 고체로 하이드록시카복실산으로 분류된다. 2-하이드록시아이소뷰티르산은 폴리에스터의 자연 발생 전구체로 간주되어 왔다.^[2] 2-하이드록시아이소뷰티르산은 젖산(CH
3CH(OH)CO
2H)과 밀접하게 관련되어 있다.^[3]

생성[편집]

2-하이드록시아이소뷰티릴 조효소 A(CoA) 뮤테이스는 3-하이드록시뷰티릴 조효소 A를 2-하이드록시아이소뷰티릴 조효소 A로 이성질화한다. 2-하이드록시아이소뷰티릴 조효소 A를 가수분해하면 2-하이드록시아이소뷰티르산이 생성된다.^[4]

2-하이드록시아이소뷰티르산과 리신 잔기의 ε-아미노기로부터 형성된 아마이드는 번역 후 변형의 일종이다.^[5]^[6]

에틸 메타크릴레이트(산업적으로 중요한 단량체이며 메타크릴산의 에스터)는 겉보기 탈수 반응에서 2-하이드록시아이소뷰티르산의 에틸 에스터를 오염화 인으로 처리하여 처음으로 얻었다.^[7]

같이 보기[편집]

3-하이드록시아이소뷰티르산

각주[편집]

↑ W.P.J.Gaykema; J.A.Kanters; G.Roelofsen (1978), Cryst. Struct. Commun., 47: 463
↑ Bhatia, Shashi Kant; Bhatia, Ravi Kant; Yang, Yung-Hun (2016). “Biosynthesis of Polyesters and Polyamide Building Blocks Using Microbial Fermentation and Biotransformation”. 《Reviews in Environmental Science and Bio/Technology》 15 (4): 639–663. doi:10.1007/s11157-016-9415-9. S2CID 88561532.
↑ Miltenberger, Karlheinz (2000), 〈Hydroxycarboxylic Acids, Aliphatic〉, 《울만 공업화학 백과사전(Ullmann's Encyclopedia of Industrial Chemistry)》, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_507
↑ Rohde, Maria-Teresa; Tischer, Sylvi; Harms, Hauke; Rohwerder, Thore (2017). “Production of 2-Hydroxyisobutyric Acid from Methanol by Methylobacterium extorquens AM1 Expressing ( R )-3-Hydroxybutyryl Coenzyme A-Isomerizing Enzymes”. 《Applied and Environmental Microbiology》 83 (3). Bibcode:2017ApEnM..83E2622R. doi:10.1128/AEM.02622-16. PMC 5244315. PMID 27836853.
↑ Dai, Lunzhi; Peng, Chao; Montellier, Emilie; Lu, Zhike; Chen, Yue; Ishii, Haruhiko; Debernardi, Alexandra; Buchou, Thierry; Rousseaux, Sophie; Jin, Fulai; Sabari, Benjamin R.; Deng, Zhiyou; Allis, C David; Ren, Bing; Khochbin, Saadi; Zhao, Yingming (2014). “Lysine 2-Hydroxyisobutyrylation is a Widely Distributed Active Histone Mark”. 《Nature Chemical Biology》 10 (5): 365–370. doi:10.1038/nchembio.1497. PMID 24681537.
↑ Carrola, Joana; Rocha, CláUdia M.; Barros, António S.; Gil, Ana M.; Goodfellow, Brian J.; Carreira, Isabel M.; Bernardo, João; Gomes, Ana; Sousa, Vitor; Carvalho, Lina; Duarte, Iola F. (2011). “Metabolic Signatures of Lung Cancer in Biofluids: NMR-Based Metabonomics of Urine”. 《Journal of Proteome Research》 10 (1): 221–230. doi:10.1021/pr100899x. PMID 21058631.
↑ E. Frankland, B. F. Duppa (1865). “Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe”. 《Justus Liebigs Annalen der Chemie》 136: 12. doi:10.1002/jlac.18651360102.

[1] W.P.J.Gaykema; J.A.Kanters; G.Roelofsen (1978), Cryst. Struct. Commun., 47: 463

[2] Bhatia, Shashi Kant; Bhatia, Ravi Kant; Yang, Yung-Hun (2016). “Biosynthesis of Polyesters and Polyamide Building Blocks Using Microbial Fermentation and Biotransformation”. 《Reviews in Environmental Science and Bio/Technology》 15 (4): 639–663. doi:10.1007/s11157-016-9415-9. S2CID 88561532.

[3] Miltenberger, Karlheinz (2000), 〈Hydroxycarboxylic Acids, Aliphatic〉, 《울만 공업화학 백과사전(Ullmann's Encyclopedia of Industrial Chemistry)》, Weinheim: Wiley-VCH, doi:10.1002/14356007.a13_507

[4] Rohde, Maria-Teresa; Tischer, Sylvi; Harms, Hauke; Rohwerder, Thore (2017). “Production of 2-Hydroxyisobutyric Acid from Methanol by Methylobacterium extorquens AM1 Expressing ( R )-3-Hydroxybutyryl Coenzyme A-Isomerizing Enzymes”. 《Applied and Environmental Microbiology》 83 (3). Bibcode:2017ApEnM..83E2622R. doi:10.1128/AEM.02622-16. PMC 5244315. PMID 27836853.

[5] Dai, Lunzhi; Peng, Chao; Montellier, Emilie; Lu, Zhike; Chen, Yue; Ishii, Haruhiko; Debernardi, Alexandra; Buchou, Thierry; Rousseaux, Sophie; Jin, Fulai; Sabari, Benjamin R.; Deng, Zhiyou; Allis, C David; Ren, Bing; Khochbin, Saadi; Zhao, Yingming (2014). “Lysine 2-Hydroxyisobutyrylation is a Widely Distributed Active Histone Mark”. 《Nature Chemical Biology》 10 (5): 365–370. doi:10.1038/nchembio.1497. PMID 24681537.

[6] Carrola, Joana; Rocha, CláUdia M.; Barros, António S.; Gil, Ana M.; Goodfellow, Brian J.; Carreira, Isabel M.; Bernardo, João; Gomes, Ana; Sousa, Vitor; Carvalho, Lina; Duarte, Iola F. (2011). “Metabolic Signatures of Lung Cancer in Biofluids: NMR-Based Metabonomics of Urine”. 《Journal of Proteome Research》 10 (1): 221–230. doi:10.1021/pr100899x. PMID 21058631.

[7] E. Frankland, B. F. Duppa (1865). “Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe”. 《Justus Liebigs Annalen der Chemie》 136: 12. doi:10.1002/jlac.18651360102.

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