7-hydroxy-L-tryptophan

Base Information

• Chemical Name: 7-hydroxy-L-tryptophan
• CAS No.: 25198-02-1
• Molecular Formula: C11H12N2O3
• Molecular Weight: 220.228
• DSSTox Substance ID: DTXSID70431948
• Nikkaji Number: J1.886.842C
• Wikidata: Q27121622
• Mol file: 25198-02-1.mol

Synonyms:7-hydroxy-L-tryptophan;25198-02-1;L-Tryptophan, 7-hydroxy-;(S)-2-Amino-3-(7-hydroxy-1H-indol-3-yl)propanoic acid;(2S)-2-amino-3-(7-hydroxy-1H-indol-3-yl)propanoic acid;Tryptophan, 7-hydroxy-;SCHEMBL1460650;CHEBI:49348;DTXSID70431948;Q27121622

Chemical Property of 7-hydroxy-L-tryptophan

Chemical Property:

• PSA: 99.34000
• LogP: 1.52820
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.08479225
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 7-hydroxy-L-tryptophan

There total 2 articles about 7-hydroxy-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: 10.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 7-Hydroxy-L-tryptophan (25198-02-1) + 4-Hydroxy-L-tryptophan (25242-90-4) + (S)-6-hydroxytryptophan (13567-14-1,1398507-94-2) + L-5-HTP (4350-09-8,4298-20-8)

Guidance literature:

With dihydrogen peroxide; edetate disodium; iron(II) sulfate; ascorbic acid; In water; at 22 ℃; for 0.0416667h;

Reference yield:

7-Indolol (2380-84-9) + L-serin (56-45-1,83245-15-2) → 7-Hydroxy-L-tryptophan (25198-02-1)

Guidance literature:

With transformed Escherichia coli cells; at 37 ℃; for 4h;

Reference yield:

7-Hydroxy-L-tryptophan (25198-02-1) → psilocybin (520-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Psilocybe cubensis enzymes PsiD / aq. buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction

2: ATP / aq. buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction

3: Psilocybe cubensis enzymes PsiM / aq. buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction

With ATP; In aq. buffer;

DOI:10.1002/chem.201801047

upstream raw materials:

7-Indolol

L-serin

L-Tryptophan

Downstream raw materials:

psilocybin

Refernces

• 1、 Berg, E. M. M. van den,Jansen, F. J. H. M.,Goede, A. T. J. W. de,Baldew, A. U.,Lugtenburg, J.. "Chemo-enzymatic synthesis and characterization of L-tryptophans selectively 13C-enriched or hydroxylated in the six-membered ring using transformed Escherichia coli cells". . p. 287 - 297. Retrieved 2007/10/02.