2-氨基异丁酸

2-氨基异丁酸
	IUPAC名; 2-Amino-2-methylpropanoic acid; 2-氨基-2-甲基丙酸
别名	α-氨基异丁酸; 2-甲基丙氨酸
识别
CAS号	62-57-7
PubChem	6119
ChemSpider	5891
SMILES	O=C(O)C(N)(C)C;
InChI	1/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7);
InChIKey	FUOOLUPWFVMBKG-UHFFFAOYAD
ChEBI	27971
DrugBank	DB02952
KEGG	C03665
性质
化学式	C4H9NO2
摩尔质量	103.12 g·mol−1
外观	白色结晶粉末
密度	1.09 g/mL
沸点	204.4 °C（478 K）
溶解性（水）	易溶
pKa	2.36 (羧基; H2O); 10.21 (氨基; H2O);
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2-氨基异丁酸，也称为α-氨基异丁酸、AIB、α-甲基丙氨酸或2-甲基丙氨酸，是一种非蛋白氨基酸，结构式为H₂N-C(CH₃)₂-COOH。它在自然界中很罕见，仅在陨石和一些真菌来源的抗生素中（如丙甲菌素（英语：Alamethicin）和一些羊毛硫抗生素（英语：Lantibiotics））发现。^[2]

合成[编辑]

在实验室中，2-氨基异丁酸可以由丙酮氰醇通过与氨反应然后水解来制备。^[3]工业规模的合成可以通过甲基丙烯酸的选择性氢胺化（英语：Hydroamination）来实现。

生物活性[编辑]

2-氨基异丁酸不是蛋白氨基酸之一，并且在自然界中相当罕见（参见非蛋白氨基酸）。由于其偕二甲基基团的索普-英戈尔德效应，它是肽中强螺旋诱导剂。^[4]2-氨基异丁酸低聚物形成3₁₀螺旋。

核糖体掺茹肽[编辑]

2-氨基异丁酸与肽合成的核糖体延伸相容。加藤等人使用Flexizyme^[5]和工程化的tRNA体来增强氨酰化AIB-tRNA物种与延伸因子P（英语：Elongation factor P）的亲和力。^[6]结果是在无细胞翻译系统中2-氨基异丁酸与肽的结合增加。伊克巴尔等人使用另一种方法来创建编辑缺陷型缬氨酸—tRNA连接酶（英语：Valine—tRNA ligase）来合成氨酰化AIB-tRNA^Val。随后将氨酰化的tRNA用于无细胞翻译系统以产生含有2-氨基异丁酸的肽。^[7]

参考资料[编辑]

^ Haynes, William M. (编). CRC Handbook of Chemistry and Physics 97th. CRC Press. 2016: 5–88. ISBN 978-1498754286.
^ Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms. Science News. 23 July 2020 [24 July 2020].
^ (1931) "α-Aminoisobutyric acid". Org. Synth. 11: 4; Coll. Vol. 2: 29. .
^ Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution). Biopolymers. 2001, 60 (6): 396–419. ISSN 0006-3525. PMID 12209474. doi:10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7.
^ Ohuchi, Masaki; Murakami, Hiroshi; Suga, Hiroaki. The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus. Current Opinion in Chemical Biology. 2007, 11 (5): 537–542. PMID 17884697. doi:10.1016/j.cbpa.2007.08.011.
^ Katoh, Takayuki; Iwane, Yoshihiko; Suga, Hiroaki. Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation. Nucleic Acids Research. 2017-12-15, 45 (22): 12601–12610. ISSN 0305-1048. PMC 5728406 . PMID 29155943. doi:10.1093/nar/gkx1129 （英语）.
^ Iqbal, Emil S.; Dods, Kara K.; Hartman, Matthew C. T. Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase. Organic & Biomolecular Chemistry. 2018, 16 (7): 1073–1078. ISSN 1477-0539. PMC 5993425 . PMID 29367962. doi:10.1039/c7ob02931d （英语）.

[CRC97-1] Haynes, William M. (编). CRC Handbook of Chemistry and Physics 97th. CRC Press. 2016: 5–88. ISBN 978-1498754286.

[2] Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms. Science News. 23 July 2020 [24 July 2020].

[3] (1931) "α-Aminoisobutyric acid". Org. Synth. 11: 4; Coll. Vol. 2: 29. .

[4] Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution). Biopolymers. 2001, 60 (6): 396–419. ISSN 0006-3525. PMID 12209474. doi:10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7.

[5] Ohuchi, Masaki; Murakami, Hiroshi; Suga, Hiroaki. The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus. Current Opinion in Chemical Biology. 2007, 11 (5): 537–542. PMID 17884697. doi:10.1016/j.cbpa.2007.08.011.

[6] Katoh, Takayuki; Iwane, Yoshihiko; Suga, Hiroaki. Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation. Nucleic Acids Research. 2017-12-15, 45 (22): 12601–12610. ISSN 0305-1048. PMC 5728406 . PMID 29155943. doi:10.1093/nar/gkx1129 （英语）.

[7] Iqbal, Emil S.; Dods, Kara K.; Hartman, Matthew C. T. Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase. Organic & Biomolecular Chemistry. 2018, 16 (7): 1073–1078. ISSN 1477-0539. PMC 5993425 . PMID 29367962. doi:10.1039/c7ob02931d （英语）.

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