6-fluorotryptophan

Base Information

• Chemical Name: 6-fluorotryptophan
• CAS No.: 343-92-0
• Molecular Formula: C₁₁H₁₁FN₂O₂
• Molecular Weight: 222.219
• Mol file: 343-92-0.mol

Synonyms:DL-Tryptophan,6-fluoro-; Tryptophan, 6-fluoro-, DL- (8CI); (?à)-6-Fluorotryptophan; 6-Fluoro-DL-tryptophan;6-Fluorotryptophan; DL-6-Fluorotryptophan; DL-6-Fluorotryptophane; NSC 9364

Chemical Property of 6-fluorotryptophan

Chemical Property:

• Boiling Point: 450.7°Cat760mmHg
• Flash Point: 226.4°C
• Density: 1.442g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-fluorotryptophan

There total 10 articles about 6-fluorotryptophan 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: 76.0%

6-fluoro-1H-indole (399-51-9) + L-serin (56-45-1,83245-15-2) → D-6-fluorotryptophan (108391-82-8,343-92-0)

Guidance literature:

6-fluoro-1H-indole; 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

Reference yield: 51.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 6-fluoro-1,2,3,4-tetrahydro-β-carbolin-3-carboxylic acid ethyl ester + DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1) → 7-fluoro-1,2,3,4-tetrahydro-β-carbolin-3-carboxylic acid ethyl ester + DL-6-fluorotryptophan (7730-20-3,108391-82-8,343-92-0)

Guidance literature:

In sodium hydroxide; ethanol; water; benzene;

Reference yield:

→ DL-6-fluorotryptophan (7730-20-3,108391-82-8,343-92-0)

Guidance literature:

upstream raw materials:

formaldehyd

DL-5-fluorotryptophan

N^α-acetyl-6-fluoro-D,L-tryptophan

6-fluoro-1H-indole

Downstream raw materials:

2-amino-3-(6-fluoro-1H-indol-3-yl)-propionic acid methyl ester

2-((tert-butoxycarbonyl)amino)-3-(6-fluoro-1H-indol-3-yl)propanoic acid

D-6-fluorotryptophan

t-butoxycarbonyl-DL-6-fluorotryptophan

Refernces

• 1、 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.
• 2、 Nakano, Shogo,Minamino, Yuki,Hasebe, Fumihito,Ito, Sohei. "Deracemization and stereoinversion to aromatic d-amino acid derivatives with ancestral l-amino acid oxidase". . p. 10152 - 10158. Retrieved 2019/10/19.