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{{Chembox
{{Other uses|AIB (disambiguation)}}
⚫ | Watchedfields = changed
{{chembox
⚫ | verifiedrevid = 477197928
⚫ | Verifiedfields = changed
⚫ | verifiedrevid = 456507634
| Name = 2-Aminoisobutyric acid | Name = 2-Aminoisobutyric acid
| ImageFile = 2-aminoisobutyric acid.svg | ImageFile = 2-aminoisobutyric acid.svg
| ImageSize = 170
⚫ | IUPACName = 2-Amino-2-methylpropanoic acid
| OtherNames = α-Aminoisobutyric acid<br/>2-Methylalanine | ImageFile1 = 2-Methylalanine-3D-balls.png
| ImageSize1 = 180
⚫ | Section1 = {{Chembox Identifiers
| ImageAlt1 = 2-methylalanine molecule
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PIN = 2-Amino-2-methylpropanoic acid
| OtherNames = α-Aminoisobutyric acid<br/>2-Methylalanine
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5891 | ChemSpiderID = 5891
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
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| StdInChIKey = FUOOLUPWFVMBKG-UHFFFAOYSA-N | StdInChIKey = FUOOLUPWFVMBKG-UHFFFAOYSA-N
| CASNo = 62-57-7 | CASNo = 62-57-7
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | EC-number = 200-544-0
| PubChem = 6119 | UNII = 1E7ZW41IQU
⚫ | EC_number = 200-544-0
⚫ | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = EXPT00471 | PubChem = 6119
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ }}
| DrugBank = DB02952
⚫ | Section2 = {{Chembox Properties
⚫ | C=4 | H=9 | N=1 | O=2
⚫ | MolarMass = 103.12 g/mol
| pKa=2.36 (carboxyl), 10.21 (amino)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>
}} }}
⚫ |Section2={{Chembox Properties
⚫ | C=4 | H=9 | N=1 | O=2
⚫ | MolarMass = 103.12 g/mol
| Appearance = white crystalline powder
| Solubility = soluble
| Density = 1.09 g/mL
| BoilingPtC = 204.4
| pKa= {{ubl
| 2.36 (carboxyl; H<sub>2</sub>O)
| 10.21 (amino; H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = ] | isbn = 978-1498754286 | page=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref>
}} }}
⚫ }}
'''2-Aminoisobutyric acid''', or '''α-aminoisobutyric acid''' ('''AIB''') or '''α-methylalanine''' or '''2-methylalanine''', is an ] with the ] is H<sub>2</sub>N-C(CH<sub>3</sub>)<sub>2</sub>-COOH. It is contained in some ]s of ] origin, e.g. ] and some ]s. It is not one of the ] amino acids and rather rare in nature. α-Aminoisobutyric acid is a strong helix inducer in ]s. Its oligomers form 3-10 helices.
}}
'''2-Aminoisobutyric acid''' (also known as '''α-aminoisobutyric acid''', '''AIB''', '''α-methylalanine''', or '''2-methylalanine''') is the ] with the ] H<sub>2</sub>N-C(CH<sub>3</sub>)<sub>2</sub>-COOH. It is rare in nature, having been only found in meteorites,<ref>{{cite news |title=Immune System of Humans, Other Mammals Could Struggle to Fight Extraterrestrial Microorganisms |url=http://www.sci-news.com/space/mammalian-immune-system-extraterrestrial-microorganisms-08668.html |newspaper=Science News |date=23 July 2020 |access-date=24 July 2020 }}</ref> and some ]s of ] origin, such as ] and some ]s.


==Synthesis==
In the laboratory, 2-aminoisobutyric acid may be prepared from ], by reaction with ] followed by hydrolysis.<ref>{{OrgSynth | last1 = Clarke | first1 = H. T. | last2 = Bean | first2 = H. J. | title = α-Aminoisobutyric acid | prep = cv2p0029 | year = 1931 | volume = 11 | pages = 4 | collvol = 2 | collvolpages = 29}}.</ref> In the laboratory, 2-aminoisobutyric acid may be prepared from ], by reaction with ] followed by hydrolysis.<ref>{{OrgSynth | last1 = Clarke | first1 = H. T. | last2 = Bean | first2 = H. J. | title = α-Aminoisobutyric acid | prep = cv2p0029 | year = 1931 | volume = 11 | pages = 4 | collvol = 2 | collvolpages = 29}}.</ref>
Industrial scale synthesis can be achieved by the selective ] of ].

==Biological activity==
2-Aminoisobutyric acid is not one of the ] amino acids and is rather rare in nature (''cf.'' ]). It is a strong helix inducer in ]s due to ] of its ]-di].<ref>{{Cite journal|last1=Toniolo|first1=C.|last2=Crisma|first2=M.|last3=Formaggio|first3=F.|last4=Peggion|first4=C.|date=2001|title=Control of peptide conformation by the Thorpe-Ingold effect (C alpha-tetrasubstitution)|url=https://pubmed.ncbi.nlm.nih.gov/12209474|journal=Biopolymers|volume=60|issue=6|pages=396–419|doi=10.1002/1097-0282(2001)60:6<396::AID-BIP10184>3.0.CO;2-7|issn=0006-3525|pmid=12209474}}</ref> Oligomers of AIB form ].

== Ribosomal incorporation into peptides ==
{{see also|Cell-free system|Cell-free protein synthesis}}

2-Aminoisobutyric acid is compatible with ribosomal elongation of peptide synthesis. Katoh ''et al.'' used ]s<ref>{{Cite journal|last1=Ohuchi|first1=Masaki|last2=Murakami|first2=Hiroshi|last3=Suga|first3=Hiroaki|title=The flexizyme system: a highly flexible tRNA aminoacylation tool for the translation apparatus|journal=Current Opinion in Chemical Biology|volume=11|issue=5|pages=537–542|doi=10.1016/j.cbpa.2007.08.011|pmid=17884697|year=2007}}</ref> and an engineered a tRNA body to enhance the affinity of aminoacylated AIB-tRNA species to ].<ref>{{Cite journal|last1=Katoh|first1=Takayuki|last2=Iwane|first2=Yoshihiko|last3=Suga|first3=Hiroaki|date=2017-12-15|title=Logical engineering of D-arm and T-stem of tRNA that enhances d-amino acid incorporation|journal=Nucleic Acids Research|language=en|volume=45|issue=22|pages=12601–12610|doi=10.1093/nar/gkx1129|pmid=29155943|issn=0305-1048|pmc=5728406}}</ref> The result was an increased incorporation of AIB into peptides in a cell free translation system. Iqbal ''et al.''. used an alternative approach of creating an editing deficient ] to synthesize aminoacylated AIB-tRNA<sup>Val</sup>. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.<ref>{{Cite journal|last1=Iqbal|first1=Emil S.|last2=Dods|first2=Kara K.|last3=Hartman|first3=Matthew C. T.|title=Ribosomal incorporation of backbone modified amino acids via an editing-deficient aminoacyl-tRNA synthetase|journal=Organic & Biomolecular Chemistry|volume=16|issue=7|pages=1073–1078|language=en|doi=10.1039/c7ob02931d|pmid=29367962|pmc=5993425|issn=1477-0539|year=2018}}</ref>


==References== ==References==
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{{DEFAULTSORT:Aminoisobutyric acid, 2-}} {{DEFAULTSORT:Aminoisobutyric acid, 2-}}
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Latest revision as of 11:49, 18 September 2023

2-Aminoisobutyric acid
2-methylalanine molecule
Names
Preferred IUPAC name 2-Amino-2-methylpropanoic acid
Other names α-Aminoisobutyric acid
2-Methylalanine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.495 Edit this at Wikidata
EC Number
  • 200-544-0
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)Key: FUOOLUPWFVMBKG-UHFFFAOYSA-N
  • InChI=1/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)Key: FUOOLUPWFVMBKG-UHFFFAOYAD
SMILES
  • O=C(O)C(N)(C)C
Properties
Chemical formula C4H9NO2
Molar mass 103.12 g/mol
Appearance white crystalline powder
Density 1.09 g/mL
Boiling point 204.4 °C (399.9 °F; 477.5 K)
Solubility in water soluble
Acidity (pKa)
  • 2.36 (carboxyl; H2O)
  • 10.21 (amino; H2O)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

2-Aminoisobutyric acid (also known as α-aminoisobutyric acid, AIB, α-methylalanine, or 2-methylalanine) is the non-proteinogenic amino acid with the structural formula H2N-C(CH3)2-COOH. It is rare in nature, having been only found in meteorites, and some antibiotics of fungal origin, such as alamethicin and some lantibiotics.

Synthesis

In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis. Industrial scale synthesis can be achieved by the selective hydroamination of methacrylic acid.

Biological activity

2-Aminoisobutyric acid is not one of the proteinogenic amino acids and is rather rare in nature (cf. non-proteinogenic amino acids). It is a strong helix inducer in peptides due to Thorpe–Ingold effect of its gem-dimethyl group. Oligomers of AIB form 310 helices.

Ribosomal incorporation into peptides

See also: Cell-free system and Cell-free protein synthesis

2-Aminoisobutyric acid is compatible with ribosomal elongation of peptide synthesis. Katoh et al. used flexizymes and an engineered a tRNA body to enhance the affinity of aminoacylated AIB-tRNA species to elongation factor P. The result was an increased incorporation of AIB into peptides in a cell free translation system. Iqbal et al.. used an alternative approach of creating an editing deficient valine—tRNA ligase to synthesize aminoacylated AIB-tRNA. The aminoacylated tRNA was subsequently used in a cell-free translation system to yield AIB-containing peptides.

References

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