6-chlorotryptophan

Base Information

• Chemical Name: 6-chlorotryptophan
• CAS No.: 17808-35-4
• Molecular Formula: C₁₁H₁₁ClN₂O₂
• Molecular Weight: 238.674
• Mol file: 17808-35-4.mol

Synonyms:DL-Tryptophan,6-chloro-; Tryptophan, 6-chloro-, DL- (8CI); 6-Chloro-DL-tryptophan;6-Chlorotryptophan; DL-6-Chlorotryptophan; DL-6-Chlorotryptophane

Chemical Property of 6-chlorotryptophan

Chemical Property:

• Boiling Point: 476.9°Cat760mmHg
• Flash Point: 242.2°C
• Density: 1.474g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chlorotryptophan

There total 40 articles about 6-chlorotryptophan 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: 98.0%

6-chloroindole (17422-33-2) + L-serin (56-45-1,83245-15-2) → 6-chloro-DL-tryptophan (33468-35-8,17808-35-4)

Guidance literature:

With Pf₀A₉ enzyme; In aq. phosphate buffer; water; dimethyl sulfoxide; at 75 ℃; for 12h; pH=8; Enzymatic reaction;

DOI:10.1021/jacs.7b05007

Reference yield: 96.0%

6-chloro-L-tryptophan ethyl ester (769973-16-2) → 6-chloro-DL-tryptophan (33468-35-8,17808-35-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; at 40 ℃; for 1h;

DOI:10.1081/SCC-200026636

Reference yield: 63.0%

methyl 2-amino-3-(6-chloro-1H-indol-3-yl)propanoate hydrochloride → 6-chloro-DL-tryptophan (33468-35-8,17808-35-4)

Guidance literature:

With water; α-chymotrypsin; In dimethyl sulfoxide; for 22h; pH=5.5; optical yield given as %ee; aq. sodium citrate buffer; Enzymatic reaction;

DOI:10.1016/j.bmc.2009.01.039

upstream raw materials:

(6-chloro-indol-3-ylmethyl)-formylamino-malonic acid diethyl ester

N-Formyl-6-chlortryptophan

6-chloroindole

1-(6-chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Downstream raw materials:

D-6-chlorotryptophan

L-4-chlorokynurenine

2-(6-chloro-1H-indole-3-yl)ethan-1-amine

(S)-N-boc-6-chloro-tryptophan

Refernces

• 1、 Smith, Duncan R. M.,Uria, Agustinus R.,Helfrich, Eric J. N.,Milbredt, Daniela,Van Pée, Karl-Heinz,Piel, J?rn,Goss, Rebecca J. M.. "An Unusual Flavin-Dependent Halogenase from the Metagenome of the Marine Sponge Theonella swinhoei WA". . p. 1281 - 1287. Retrieved 2017.
• 2、 Minges, Hannah,Schnepel, Christian,B?ttcher, Dominique,Wei?, Martin S.,Spro?, Jens,Bornscheuer, Uwe T.,Sewald, Norbert. "Targeted Enzyme Engineering Unveiled Unexpected Patterns of Halogenase Stabilization". . p. 818 - 831. Retrieved 2020.
• 3、 Kemker, Isabell,Schr?der, David C.,Feiner, Rebecca C.,Müller, Kristian M.,Marion, Antoine,Sewald, Norbert. "Tuning the Biological Activity of RGD Peptides with Halotryptophans ?". . p. 586 - 601. Retrieved 2021/01/14.