4-Methoxy-L-tryptophan

Base Information

• Chemical Name: 4-Methoxy-L-tryptophan
• CAS No.: 406938-53-2
• Molecular Formula: C12H14N2O3
• Molecular Weight: 234.255
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60459116
• Wikidata: Q27451438
• Mol file: 406938-53-2.mol

Synonyms:406938-53-2;(S)-2-Amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid;4-METHOXY-L-TRYPTOPHAN;L-Tryptophan, 4-methoxy-;(2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid;Tryptophan, 4-methoxy-;4-methoxytryptophane;SCHEMBL1461064;(S)-2-Amino-3-(4-methoxy-1H-indol-3-yl)propanoicacid;DTXSID60459116;CS-D1293;MFCD17214440;AKOS016843465;DS-18031;Q27451438;(S)-2-Amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid (H-L-Trp(4-OMe)-OH)

Chemical Property of 4-Methoxy-L-tryptophan

Chemical Property:

• PSA: 88.34000
• LogP: 1.83120
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 234.10044231
• Heavy Atom Count: 17
• Complexity: 285

Purity/Quality:

97% ^*data from raw suppliers

(S)-2-Amino-3-(4-methoxy-1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C1C(=CN2)CC(C(=O)O)N
• Isomeric SMILES: COC1=CC=CC2=C1C(=CN2)C[C@@H](C(=O)O)N

Technology Process of 4-Methoxy-L-tryptophan

There total 11 articles about 4-Methoxy-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: 47.0%

4-methoxy-1H-indole (4837-90-5) + L-serin (56-45-1,83245-15-2) → 4-methoxy-L-tryptophan (406938-53-2,199540-73-3)

Guidance literature:

With Thermotoga maritime recombinant tryptophan synthase; In aq. phosphate buffer; at 80 ℃; for 24h; pH=7.5; Inert atmosphere; Enzymatic reaction;

DOI:10.1021/ja310734n

Reference yield:

zelkovamycin E → D-Alanine (338-69-2,25191-17-7,18875-37-1) + (R)-2-aminobutyric acid (2623-91-8) + 2-((R)-1-Amino-ethyl)-thiazole-4-carboxylic acid + 4-methoxy-L-tryptophan (406938-53-2,199540-73-3)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 1h;

DOI:10.1021/acs.orglett.0c03565

Reference yield:

zelkovamycin D → (R)-2-aminobutyric acid (2623-91-8) + 4-methoxy-L-tryptophan (406938-53-2,199540-73-3)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 1h;

DOI:10.1021/acs.orglett.0c03565

upstream raw materials:

3-(4-methoxy-1H-indol-3-yl)-2-phenylacetylaminopropionic acid

4-methoxy-1H-indole

(4-methoxy-1H-indol-3-ylmethyl)dimethylamine

diethyl 2-(4-methoxy-1H-indol-3-ylmethyl)-2-phenylacetylaminomalonate

Downstream raw materials:

N^α-Cbz-(4-OMe)Trp-Gly-OMe

N^α-Cbz-Trp-(4-OMe)Trp-Gly-OMe

Cyclo[D-AlaThz-L-Trp-L-(4-OMe)Trp-Gly-D-Aby-L-(Ph)Sec-Sar]

N-Boc-D-AlaThz-Trp-(4-OMe)Trp-Gly-D-Abu-(Ph)Sec-Sar-OEt