(2R)-2-ammonio-3-methylbutanoate

Base Information

• Chemical Name: (2R)-2-ammonio-3-methylbutanoate
• CAS No.: 640-68-6
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 2922.49
• Mol file: 640-68-6.mol

Synonyms:(2R)-2-ammonio-3-methylbutanoate;(2R)-2-azaniumyl-3-methyl-butanoate;D-valine zwitterion;D-2-amino-3-methylbutyric acid;CHEBI:74338;2-Amino-3-methylbutanoic acid(D);A828684;A834630

Chemical Property of (2R)-2-ammonio-3-methylbutanoate

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.0633mmHg at 25°C
• Melting Point: >295 °C (subl.)(lit.)
• Refractive Index: -27 ° (C=8, 6mol/L HCl)
• Boiling Point: 213.6 °C at 760 mmHg
• PKA: 2.37±0.10(Predicted)
• Flash Point: 83 °C
• PSA: 63.32000
• Density: 1.063 g/cm³
• LogP: 0.75460
• Storage Temp.: Store at RT.
• Solubility.: 56 g/L (20°C)
• Water Solubility.: 56 g/L (20 ºC)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 84.9

Purity/Quality:

99.4% ^*data from raw suppliers

D-Valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC(C)[C@H](C(=O)[O-])[NH3+]
• General Description: D-Valine, also known as (R)-Valine or (2R)-2-amino-3-methylbutanoic acid, is an enantiomer of L-valine and serves as a key component in the formation of stable left-handed 310-helices when incorporated into peptide sequences with an all-R configuration. Its structural role in peptide helices highlights its utility in designing peptidomimetics and scaffolds with predictable secondary structures, as demonstrated by its ability to stabilize helical conformations in both solid state and solution.

Technology Process of (2R)-2-ammonio-3-methylbutanoate

There total 127 articles about (2R)-2-ammonio-3-methylbutanoate 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: 80.0%

4-<(2R,5S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl>butylamine (129243-87-4) → D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + L-Lysine hydrochloride (657-27-2,10098-89-2,26124-78-7)

Guidance literature:

With hydrogenchloride; at 70 ℃;

Reference yield:

itralamide B (1187486-25-4) → N-methylalanine (3913-67-5) + D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (2S,3R)-3-hydroxy-2-(methylamino)butanoic acid (2812-28-4) + N-methylalanylvaline + N-methylphenylalanylvaline + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 18.5h;

DOI:10.1021/np900173d

Reference yield:

(4aS,10aR,13S,19aR,21aS,26bR,27aS,30R)-24-chloro-2,3,4,4a,8,9,10,10a,12,13,17,18,19,19a,22,26b,27,27a,29,30-icosahydro-25,26b-dihydroxy-12,13-dimethyl-30-(propan-2-yl)-7H,21aH-tripyridazino[1’’,6’’:10’,11’;1’’’,6’’’:16’,17’;1’’’’,6’’’’:7’,8’] [1,4,7,10,13,16]hexaazacyclooctadecino[1’,2’:1,5]pyrrolo[2,3-b]indole-5,11,14,20,28,31(1H,16H)-hexone (1400276-81-4) → N-methyl-D-alanine (29475-64-7) + D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (2S,3aR,8aR)-6-chloro-1,2,3,3a,8,8a-hexahydro-3a,5-dihydroxypyrrolo-[2,3-b]indole-2-carboxylic acid + (3S)-hexahydropyridazine-3-carboxylic acid

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1002/cbdv.201100364

upstream raw materials:

D,L-valine

N-formylvaline

N-chloroacetyl-D-valine

2-iodo-propane

Downstream raw materials:

N-(N-benzoyl-D-valyl)-D-valine

N-(N-benzoyl-L-valyl)-D-valine

(R)-2-Hydroxy-3-methylbutyric acid

N-[(benzyloxy)carbonyl]-D-valine

Refernces

Stable right- and left-handed peptide helices containing C ^α-tetrasubstituted α-amino acids

10.1021/jo900222g

The study investigates the synthesis and structural properties of stable peptide helices incorporating CR-tetrasubstituted R-amino acids, specifically focusing on the unnatural amino acid rac-14. The researchers synthesized 13 different peptides with lengths up to eight residues, using alternating sequences of rac-14 and (S)- or (R)-valine. The peptides were characterized by X-ray diffraction, NMR, and CD measurements. The results showed that peptides with an all-S backbone configuration formed right-handed 310-helices, while those with an all-R configuration formed left-handed 310-helices in both solid state and solution. The study demonstrates the potential of these peptides as scaffolds and peptidomimetics due to their stable and predictable secondary structures.