6-Chloro-L-tryptophan

Base Information

• Chemical Name: 6-Chloro-L-tryptophan
• CAS No.: 33468-35-8
• Molecular Formula: C11H11ClN2O2
• Molecular Weight: 238.67
• Hs Code.: 2933990090
• UNII: T8BEF538ZK
• DSSTox Substance ID: DTXSID501318992
• Nikkaji Number: J703.866F
• Wikidata: Q27456335
• Mol file: 33468-35-8.mol

Synonyms:6-CHLORO-L-TRYPTOPHAN;33468-35-8;(S)-2-Amino-3-(6-chloro-1H-indol-3-yl)propanoic acid;6-Chloro L-Tryptophan;L-Tryptophan, 6-chloro-;(2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid;T8BEF538ZK;UNII-T8BEF538ZK;6-chloro-tryptophan;SCHEMBL456668;CHEBI:140077;FICLVQOYKYBXFN-VIFPVBQESA-N;DTXSID501318992;MFCD02683925;AKOS015850367;DS-4885;HY-W050025;A5961;CS-0031367;C21866;O10210;W-204220;Q27456335;(S)-2-Amino-3-(6-chloro-1H-indol-3-yl)propanoic acid (H-L-Trp(6-Cl)-OH)

Chemical Property of 6-Chloro-L-tryptophan

Chemical Property:

• Melting Point: 244-246°C
• Boiling Point: 476.906 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 242.224 °C
• PSA: 79.11000
• Density: 1.475 g/cm³
• LogP: 2.47600
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Acid (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 238.0509053
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Chloro 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=C1Cl)NC=C2CC(C(=O)O)N
• Isomeric SMILES: C1=CC2=C(C=C1Cl)NC=C2C[C@@H](C(=O)O)N
• Uses: The natural enantiomer of Chlorotryptophan The natural enantiomer of Chlorotryptophan.

Technology Process of 6-Chloro-L-tryptophan

There total 24 articles about 6-Chloro-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: 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-L-tryptophan ethyl ester

6-chloro-3-methyl-1H-indole

6-chloro-3-methylindole-2-carboxylate

tert-butyl 6-chloro-3-methyl-1H-indole-1-carboxylate

Downstream raw materials:

N-trityl-6-chloro-L-tryptophan

(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(6-chloro-1H-indol-3-yl)propanoic acid

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

L-4-chlorokynurenine

Refernces

• 1、 Luhavaya, Hanna,Sigrist, Renata,Chekan, Jonathan R.,McKinnie, Shaun M. K.,Moore, Bradley S.. "Biosynthesis of l-4-Chlorokynurenine, an Antidepressant Prodrug and a Non-Proteinogenic Amino Acid Found in Lipopeptide Antibiotics". supporting information. p. 8394 - 8399. Retrieved 2019/05/21.
• 2、 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 2017/05/29.