(R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid
• CAS No.: 110221-04-0
• Molecular Formula: C₁₁H₁₁FN₂O₂
• Molecular Weight: 222.219
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID10350902
• Nikkaji Number: J369.728B
• Mol file: 110221-04-0.mol

Synonyms:110221-04-0;(R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid;4-Fluoro-D-tryptophan;(2R)-2-amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid;(R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoicacid;DTXSID10350902;CS-0440809;A50406

Chemical Property of (R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid

Chemical Property:

• Boiling Point: 450.7±45.0 °C(Predicted)
• PKA: 2.19±0.10(Predicted)
• Density: 1.442±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.08045576
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%min ^*data from raw suppliers

(R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)F)C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C(=C1)F)C(=CN2)C[C@H](C(=O)O)N

Technology Process of (R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid

There total 11 articles about (R)-2-Amino-3-(4-fluoro-1H-indol-3-yl)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: 97.0%

4-fluoroindole (387-43-9) + L-serin (56-45-1,83245-15-2) → (S)-2-amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid (110221-04-0,25631-17-8)

Guidance literature:

With Tm₂F₃ enzyme; In aq. phosphate buffer; water; dimethyl sulfoxide; at 75 ℃; for 12h; pH=8; Enzymatic reaction;

DOI:10.1021/jacs.7b05007

Reference yield: 82.0%

(S)-1-tosyl-4-fluorotryptophan methyl ester (1369571-01-6) → (S)-2-amino-3-(4-fluoro-1H-indol-3-yl)propanoic acid (110221-04-0,25631-17-8)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 0.5h; Reflux;

DOI:10.1080/00397911.2010.523154

Reference yield: 68.0%

4-fluoroindole (387-43-9) + L-serin (56-45-1,83245-15-2) → C11H11FN2O2 (110221-04-0,25631-17-8)

Guidance literature:

4-fluoroindole; L-serin; With Salmonella enterica tryptophan synthase; In methanol; aq. phosphate buffer; at 37 ℃; pH=8.0; Enzymatic reaction;

With (2R)-aspartic acid; In methanol; aq. phosphate buffer; pH=8.0;

In aq. phosphate buffer; deuteromethanol; at 37 ℃; pH=8.0; stereoselective reaction; Enzymatic reaction;

DOI:10.1021/acscatal.9b00739

upstream raw materials:

4-fluoroindole

L-serin

[4-fluoro-1-(4-toluenesulfonyl)indol-3-yl]carboxaldehyde

(S)-1-tosyl-4-fluorotryptophan methyl ester

Downstream raw materials:

C₁₁H₁₁FN₂O₂

Refernces

• 1、 Winn, Michael,Francis, Daniel,Micklefield, Jason. "De novo Biosynthesis of “Non-Natural” Thaxtomin Phytotoxins". . p. 6830 - 6833. Retrieved 2018.
• 2、 Bunn, Brittney M,Xu, Mizhi,Webb, Chase M,Viswanathan, Rajesh. "Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA". . . Retrieved 2021/04/26.
• 3、 Parmeggiani, Fabio,Rué Casamajo, Arnau,Walton, Curtis J. W.,Galman, James L.,Turner, Nicholas J.,Chica, Roberto A.. "One-Pot Biocatalytic Synthesis of Substituted d -Tryptophans from Indoles Enabled by an Engineered Aminotransferase". . p. 3482 - 3486. Retrieved 2019/04/13.