4-Bromo-L-tryptophan

Base Information

• Chemical Name: 4-Bromo-L-tryptophan
• CAS No.: 52448-16-5
• Molecular Formula: C11H11BrN2O2
• Molecular Weight: 283.125
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80431893
• Nikkaji Number: J870.306J
• Mol file: 52448-16-5.mol

Synonyms:52448-16-5;4-BROMO-L-TRYPTOPHAN;(S)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoic acid;(2S)-2-AMINO-3-(4-BROMO-1H-INDOL-3-YL)PROPANOIC ACID;4-bromotryptophan;(S)-2-Amino-3-(4-bromo-1H-indol-3-yl)propanoicacid;SCHEMBL7485105;DTXSID80431893;MFCD10565749;AKOS016843466;4-Bromo-L-tryptophan (H-L-Trp(4-Br)-OH);A870985

Chemical Property of 4-Bromo-L-tryptophan

Chemical Property:

• PSA: 79.11000
• LogP: 2.58510
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 282.00039
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%Min ^*data from raw suppliers

4-Bromo-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C(=C1)Br)C(=CN2)C[C@@H](C(=O)O)N
• Uses: 4-Bromo-L-tryptophan, is a fluorescent amino acid deirvative used in synthesis of fluorescent proteins used widely in biological spectroscopy and microscopy.

Technology Process of 4-Bromo-L-tryptophan

There total 14 articles about 4-Bromo-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: 91.6%

(S)-2-benzamido-3-(4-bromo-1H-indol-3-yl)propanoic acid ethyl ester → (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5)

Guidance literature:

With hydrogenchloride; In water; at 90 - 100 ℃; for 19h;

Reference yield: 72.0%

4-bromo-1H-indole (52488-36-5) + L-serin (56-45-1,83245-15-2) → (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5)

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: 47.0%

N-acetyl-4-bromo-DL-tryptophan (252026-08-7) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-2-amino-3-(4-bromo-1H-indol-3-yl)propanoic acid (52448-16-5) + (R)-N-acetyl-4-bromotryptophan methyl ester (343846-36-6)

Guidance literature:

N-acetyl-4-bromo-DL-tryptophan; With acylase from Aspergillus genus; cobalt(II) chloride; In phosphate buffer; at 37 ℃; for 48h; pH=7.51;

diazomethyl-trimethyl-silane; In methanol; hexane; ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.3987/COM-00-9137

upstream raw materials:

N-acetyl-4-bromo-DL-tryptophan

diazomethyl-trimethyl-silane

(S)-4-bromo-N-(tert-butoxycarbonyl)tryptophan methyl ester

4-bromo-1H-indole

Downstream raw materials:

(-)-trans-clavicipitic acid

L-Tryptophan

Refernces

• 1、 -. "Preparation method of non-natural L - tryptophan derivative". . . Retrieved 2021/11/21.
• 2、 Winn, Michael,Francis, Daniel,Micklefield, Jason. "De novo Biosynthesis of “Non-Natural” Thaxtomin Phytotoxins". supporting information. p. 6830 - 6833. Retrieved 2018/06/04.