L-norvaline

Base Information

• Chemical Name: L-norvaline
• CAS No.: 6600-40-4
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29224995
• Mol file: 6600-40-4.mol

Synonyms:L-Norvaline (9CI);Norvaline, L-;L-2-Aminovaleric acid;L-2-aminopentanoate;(S)-2-Aminopentanoic acid;L-(+)-2-aminovaleric acid;L-2-aminopentanoic acid;(2S)-2-aminopentanoic acid;alpha-L-Aminopentanoic acid;Leucine,2-methyl-;Pentanoic acid, 2-amino-, (S)-;L-Norvaaline;L(+)-Norvaline;(S)-2-Amino-pentanoic acid;

Chemical Property of L-norvaline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0366mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 25 ° (C=10, 6mol/L HCl)
• Boiling Point: 222.9 °C at 760 mmHg
• PKA: 2.32(at 25℃)
• Flash Point: 88.6 °C
• PSA: 63.32000
• Density: 1.067 g/cm³
• LogP: 0.89870
• Storage Temp.: Store at RT.
• Solubility.: 48.7g/l
• Water Solubility.: 10.5 g/100 mL (18 ºC)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 77

Purity/Quality:

≥98.0% ^*data from raw suppliers

L-Norvaline, 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xn
• Hazard Codes: C,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: CCC[C@@H](C(=O)[O-])[NH3+]
• General Description: L-Norvaline is a non-proteinogenic amino acid with the chemical name (S)-2-aminopentanoic acid, characterized by a five-carbon side chain. It has been synthesized stereoselectively through efficient, chromatography-free methods, demonstrating its relevance in organic and bioorganic chemistry. L-norvaline's structural features, such as its side chain length, influence molecular interactions, as seen in studies on peptide nucleic acids (PNAs), where norvalyl derivatives were used to investigate pairing selectivity and stacking properties. This highlights its utility in designing modified biomolecules for applications in molecular recognition and synthetic biology.

Technology Process of L-norvaline

There total 75 articles about L-norvaline 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: 93.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-55-0) → L-Norvaline (6600-40-4,498-18-0)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 21h; under 2068.6 Torr;

DOI:10.1021/ja00213a031

Reference yield: 92.0%

(1S,2S,5S,9S)-2,10,10-Trimethyl-5-propyl-3-oxa-6-aza-tricyclo[7.1.1.02,7]undec-6-en-4-one (141895-39-8) → L-Norvaline (6600-40-4,498-18-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 70 ℃; for 3h;

DOI:10.1016/S0957-4166(00)80263-3

Reference yield: 84.1%

2-oxopentanoic acid (1821-02-9) → L-Norvaline (6600-40-4,498-18-0)

Guidance literature:

With sodium formate; ammonium chloride; NADH; In aq. phosphate buffer; at 25 ℃; for 6h; pH=8.0; Reagent/catalyst; Kinetics; Green chemistry; Enzymatic reaction;

DOI:10.1002/cbic.201700493

upstream raw materials:

N-formyl-D,L-norvaline

N-formyl-L-norvaline

N-acetylnorvaline

N-Chloroacetyl norvaline

Downstream raw materials:

N-Acetyl-L-2-aminopentanoic acid

N-(2,4-dinitro-phenyl)-L-norvaline

methyl L-norvalinate hydrochloride

N-tert-butoxycarbonyl-L-norvaline

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.

Stereoselective Synthesis of syn -γ-Hydroxynorvaline and Related α-Amino Acids

10.1055/s-0039-1690705

The study presents a stereoselective synthesis method for three enantiomerically pure non-proteinogenic amino acids: L-norvaline, γ-oxonorvaline, and syn-γ-hydroxynorvaline. These amino acids were synthesized using a chromatography-free route that leverages a highly diastereoselective crystallization-driven Mannich reaction. Key chemicals used in the study include acetone, glyoxylic acid monohydrate, and (S)-(4-methoxyphenyl)ethylamine, which serve as readily available building blocks for the synthesis. The process involves chemoselective and stereoselective reductions of a key intermediate, amino ketone 4, to access the target amino acids. The study highlights the use of inexpensive reagents, simple protocols, and excellent selectivity, with no need for chromatography, making it an efficient and environmentally friendly approach to synthesize these biologically significant compounds.