(R)-2-Amino-3-(m-tolyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(m-tolyl)propanoic acid
• CAS No.: 114926-39-5
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID601312961
• Nikkaji Number: J524.383A
• Mol file: 114926-39-5.mol

Synonyms:114926-39-5;(R)-2-Amino-3-(m-tolyl)propanoic acid;3-Methyl-D-phenylalanine;D-3-Methylphenylalanine;(2R)-2-amino-3-(3-methylphenyl)propanoic acid;D-PHENYLALANINE, 3-METHYL-;D-3-METHYLPHE;3-Methy-D-Phenylalanine;(R)-2-Amino-3-(m-tolyl)propanoicacid;D-3-Methyl Phenylalanine;SCHEMBL1795728;JZRBSTONIYRNRI-SECBINFHSA-N;DTXSID601312961;MFCD01860871;AKOS016843520;AC-9922;AM83419;CS-W017263;HY-W016547;PS-12171;A13012;D-3-Methylphenylalanine (H-D-Phe(3-Me)-OH);EN300-199890;F12207

Chemical Property of (R)-2-Amino-3-(m-tolyl)propanoic acid

Chemical Property:

• Vapor Pressure: 8.9E-05mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 322.8 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 149 °C
• PSA: 49.33000
• Density: 1.165 g/cm³
• LogP: 1.95300
• Storage Temp.: Store at -15°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Methyl-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)CC(C(=O)O)N
• Isomeric SMILES: CC1=CC(=CC=C1)C[C@H](C(=O)O)N
• Uses: 3-Methyl-D-phenylalanine is a derivative of D-Phenylalanine (P319410) and is used as a reagent in the synthesis of aminophenylpropanyl phosphate derivatives which can exhibit pin1 inhibitory activity. 3-Methyl-D-phenylalanine is also used in the preparation of N-arylaminonitriles which are useful as bioavailable peptidomimetic inhibitors of cathepsin B.

Technology Process of (R)-2-Amino-3-(m-tolyl)propanoic acid

There total 8 articles about (R)-2-Amino-3-(m-tolyl)propanoic 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: 95.0%

2-(Benzhydrylidene-amino)-3-m-tolyl-propionic acid methyl ester (145243-34-1) → (R)-2-amino-3-(3-methylphenyl)propionic acid (114926-39-5,2283-42-3)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00056a033

Reference yield:

3-methyl-phenylalanine (5472-70-8,2283-42-3) → (R)-2-amino-3-(3-methylphenyl)propionic acid (114926-39-5,2283-42-3)

Guidance literature:

With phenylalanine ammonia-lyase from Petroselinum crispum; In aq. buffer; at 30 ℃; for 168h; pH=8.5; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

Reference yield:

3-methyl-phenylalanine (5472-70-8,2283-42-3) → (R)-2-amino-3-(3-methylphenyl)propionic acid (114926-39-5,2283-42-3) + (S)-2-amino-3-(3-methylphenyl)propionic acid (2283-42-3)

Guidance literature:

With phenylalanine ammonia-lyase from Petroselinum crispum; In aq. buffer; at 30 ℃; for 17h; pH=8.5; Reagent/catalyst; Time; stereoselective reaction; Resolution of racemate;

DOI:10.1016/j.cattod.2020.04.002

upstream raw materials:

2-(Benzhydrylidene-amino)-3-m-tolyl-propionic acid methyl ester

1-bromomethyl-3-methyl-benzene

3-methyl-phenylalanine

2-oxo-3-m-tolyl-propionic acid

Downstream raw materials:

(R)-2-hydroxy-3-(3-methylphenyl)-propionic acid

(S)-2-(3-methoxycarbonylphenylamino)-3-(3-methylphenyl)-propionic acid

(S)-6-[1-carboxy-2-(3-methylphenyl)-ethylamino]-phthalide

C₁₀H₁₅NO

Refernces

• 1、 Walton, Curtis J. W.,Parmeggiani, Fabio,Barber, Janet E. B.,McCann, Jenna L.,Turner, Nicholas J.,Chica, Roberto A.. "Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades". . p. 470 - 474. Retrieved 2017/12/15.
• 2、 Cox, Brad M.,Bilsborrow, Joshua B.,Walker, Kevin D.. "Enhanced conversion of racemic α-arylalanines to (R)-β- arylalanines by coupled racemase/aminomutase catalysis". experimental part. p. 6953 - 6959. Retrieved 2009/12/25.