alpha-Aminobutyric acid

Base Information

• Chemical Name: alpha-Aminobutyric acid
• CAS No.: 2835-81-6
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.121
• Hs Code.: 29224995
• NCI Thesaurus Code: C81116
• Metabolomics Workbench ID: 142548
• Mol file: 2835-81-6.mol

Synonyms:(2S)-2-aminobutanoic acid;2-aminobutanoic acid;2-aminobutyric acid;alpha-aminobutyric acid;alpha-aminobutyric acid, (+-)-isomer;alpha-aminobutyric acid, (R)-isomer;alpha-aminobutyric acid, (S)-isomer;butyrine;butyrine, (+-)-isomer;butyrine, (R)-isomer;butyrine, (S)-isomer;homoalanine;L-2-aminobutyric acid;l-homoalanine

Chemical Property of alpha-Aminobutyric acid

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0.135mmHg at 25°C
• Melting Point: 291 °C (dec.)(lit.)
• Refractive Index: 1.438
• Boiling Point: 215.2 °C at 760 mmHg
• PKA: 2.34±0.10(Predicted)
• Flash Point: 83.9 °C
• PSA: 63.32000
• Density: 1.105 g/cm³
• LogP: 0.50860
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 103.063328530
• Heavy Atom Count: 7
• Complexity: 66.6

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: S22:; S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C(=O)[O-])[NH3+]
• General Description: DL-2-Aminobutyric acid (also known as homoalanine) is a homolog of alanine with an extended side chain, featuring an additional methylene group. In the context of peptide nucleic acids (PNAs), its incorporation as part of the backbone (homoalanyl-PNA) influences pairing selectivity and base stacking properties due to the altered side chain length and topology. This modification demonstrates the importance of side chain homologation in fine-tuning molecular recognition and stability in PNA oligomers.

Technology Process of alpha-Aminobutyric acid

There total 65 articles about alpha-Aminobutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-Oxobutyric acid (600-18-0) → 2-aminobutanoic acid (2835-81-6) + 2-Hydroxybutanoic acid (600-15-7,565-70-8)

Guidance literature:

With water; ammonium formate; [Rh(pentamethylcyclopentadiene)(2,2'-bipyridine)H₂O]SO₄; at 80 ℃; for 1h; pH=4.5; Product distribution / selectivity;

Reference yield: 86.0%

2-Oxobutyric acid (600-18-0) → 2-aminobutanoic acid (2835-81-6)

Guidance literature:

With phenylglycin; In water; acetonitrile; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.8b03910

Reference yield: 86.0%

2-hydroxyiminobutanoic acid (609-30-3) → 2-aminobutanoic acid (2835-81-6)

Guidance literature:

With ammonium formate; zinc; In methanol; for 0.0666667h; Heating;

upstream raw materials:

2-aminobutanol

4-ethylidene-2-thioxo-thiazolidin-5-one

2-cyano-butyric acid hydrazide

2-Bromobutyric acid

Downstream raw materials:

2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid

2-Oxobutyric acid

2-(acetylamino)butanoic acid

N-benzoyl-2-aminobutyric acid

Refernces

Side chain homologation of alanyl peptide nucleic acids: Pairing selectivity and stacking

10.1039/b411545g

The study investigates the effects of side chain homologation on the pairing selectivity and stacking of alanyl peptide nucleic acids (alanyl-PNAs), which are oligomers based on a regular peptide backbone with covalently linked nucleobases. The researchers compared different linkers, such as methylene (alanyl-PNA), ethylene (homoalanyl-PNA), and trimethylene (norvalyl-PNA), to understand how side chain length influences pairing selectivity and base pair stacking. The chemicals used in the study included various nucleo amino acids, such as alanine, homoalanine, and norvaline, which were prepared and oligomerized to form different PNA sequences. These sequences were then tested for their pairing properties and stabilities, allowing the researchers to draw conclusions about the interdependence between recognition, insertion of methylene groups, and the backbone topology. The purpose of these chemical modifications was to selectively manipulate pairing selectivity and base pair stacking, providing insights into the recognition interactions and potential applications of PNAs in molecular biology.

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