6-Fluoro-L-Tryptophan

Base Information

• Chemical Name: 6-Fluoro-L-Tryptophan
• CAS No.: 19310-00-0
• Molecular Formula: C11H11FN2O2
• Molecular Weight: 222.219
• Hs Code.: 2933990090
• UNII: WB5L1P9TZO
• Nikkaji Number: J288G
• Mol file: 19310-00-0.mol

Synonyms:19310-00-0;6-Fluoro-L-Tryptophan;(S)-2-Amino-3-(6-fluoro-1H-indol-3-yl)propanoic acid;L-6-fluorotryptophan;6-Fluorotryptophan, L-;L-Tryptophan, 6-fluoro-;6F-Trp;(2S)-2-amino-3-(6-fluoro-1H-indol-3-yl)propanoic acid;WB5L1P9TZO;UNII-WB5L1P9TZO;FT6;6-Fluoro-tryptophan;SCHEMBL120340;YMEXGEAJNZRQEH-VIFPVBQESA-N;6-Fluoro-L-Tryptophan, AldrichCPR;MFCD00137731;AS-69494;PD158524;CS-0139675;A50535;EN300-11688463;Q27292541;(S)-2-Amino-3-(6-fluoro-1H-indol-3-yl)propanoicacid;(2S)-2-azaniumyl-3-(6-fluoro-1H-indol-3-yl)propanoate;(S)-2-AMINO-3-(6-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID

Chemical Property of 6-Fluoro-L-Tryptophan

Chemical Property:

• Melting Point: 262-265 °C
• Boiling Point: 450.7±45.0 °C(Predicted)
• PKA: 2.22±0.10(Predicted)
• PSA: 79.11000
• Density: 1.442±0.06 g/cm3(Predicted)
• LogP: 1.96170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -0.8
• 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:

98.5% ^*data from raw suppliers

6-Fluoro-L-Tryptophan AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)NC=C2CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C=C1F)NC=C2C[C@@H](C(=O)O)N

Technology Process of 6-Fluoro-L-Tryptophan

There total 4 articles about 6-Fluoro-L-Tryptophan 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:

Nα-acetyl-6-fluoro-D,L-tryptophan (81024-49-9) → Nα-acetyl-6-fluoro-D-tryptophan (7592-43-0) + 6-fluoro-L-tryptophan (19310-00-0,108391-82-8,343-92-0)

Guidance literature:

With cobalt(II) chloride hexahydrate; porcine kidney L-acylase; In aq. phosphate buffer; at 37 ℃; for 24h; pH=7.4; Enzymatic reaction;

DOI:10.1021/jm5002925

Reference yield:

6-fluoro-1H-indole (399-51-9) → 6-fluoro-L-tryptophan (19310-00-0,108391-82-8,343-92-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / 0.5 h / 80 °C / Microwave irradiation

2: porcine kidney L-acylase; cobalt(II) chloride hexahydrate / aq. phosphate buffer / 24 h / 37 °C / pH 7.4 / Enzymatic reaction

With cobalt(II) chloride hexahydrate; porcine kidney L-acylase; acetic acid; In aq. phosphate buffer;

DOI:10.1021/jm5002925

Reference yield:

Nα-acetyl-6-fluoro-D,L-tryptophan (81024-49-9) → Nα-acetyl-6-fluoro-D-tryptophan (7592-43-0) + Nα-acetyl-6-fluoro-L-tryptophan (7592-44-1) + 6-fluoro-L-tryptophan (19310-00-0,108391-82-8,343-92-0) + D-6-fluorotryptophan (108391-82-8,343-92-0)

Guidance literature:

With borate buffer; cobalt(II) chloride; at 37 ℃; for 48h; pH=8.0; Title compound not separated from byproducts.; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.02.120

upstream raw materials:

N^α-acetyl-6-fluoro-D,L-tryptophan

6-fluoro-1H-indole

L-serin

Downstream raw materials:

t-butoxycarbonyl-DL-6-fluorotryptophan

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

Refernces

• 1、 De Marco, Rossella,Bedini, Andrea,Spampinato, Santi,Gentilucci, Luca. "Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception". . p. 6861 - 6866. Retrieved 2014/10/15.