(2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate

Base Information

• Chemical Name: (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate
• CAS No.: 526-31-8
• Molecular Formula: C12H14 N2 O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• Mol file: 526-31-8.mol

Synonyms:(2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate;CHEBI:57283;N(alpha)-methyl-L-tryptophan zwitterion

Chemical Property of (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.74E-08mmHg at 25°C
• Melting Point: >300 °C (dec.)(lit.)
• Refractive Index: 65 ° (C=1, 0.5mol/L NaOH)
• Boiling Point: 439.1 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 219.4 °C
• PSA: 65.12000
• Density: 1.272 g/cm³
• LogP: 1.77390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

L-Abrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[NH2+]C(CC1=CNC2=CC=CC=C21)C(=O)[O-]
• Isomeric SMILES: C[NH2+][C@@H](CC1=CNC2=CC=CC=C21)C(=O)[O-]

Technology Process of (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate

There total 4 articles about (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate 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:

kyanamide → L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + L-abrine (526-31-8)

Guidance literature:

With hydrogenchloride; phenol; In water; at 110 ℃; for 16h;

DOI:10.1016/j.tet.2019.04.046

Reference yield:

S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N,N-α-dimethyl-L-tryptophan (2812-40-0) + L-abrine (526-31-8)

Guidance literature:

With recombinant (SAM)-dependent tryptophan methyltransferase from Psilocybe serbica FSU₁₂₄₁₆; In aq. buffer; at 25 ℃; for 0.25h; pH=8; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/cbic.201800336

Reference yield:

S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N,N-α-dimethyl-L-tryptophan (2812-40-0) + α-N,N,N-trimethyltryptophan betaine (64363-86-6,487-58-1,12673-47-1,97045-39-1) + L-abrine (526-31-8)

Guidance literature:

With adenine deaminase; recombinant (SAM)-dependent tryptophan methyltransferase from Psilocybe serbica FSU₁₂₄₁₆; SAH-nucleosidase; In aq. buffer; at 25 ℃; for 4h; pH=8; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/cbic.201800336

upstream raw materials:

S-adenosyl-L-methionine

L-Tryptophan

Downstream raw materials:

(1Ξ,3S)-2-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid

(+/-)-(2-indol-3-yl-1-methoxycarbonyl-ethyl)-trimethyl-ammonium; iodide

[2-(1H-indol-3-yl)-ethyl]-methylamine

N^α-(tert-butoxycarbonyl)-N^α-methyl-L-tryptophan

Refernces

• 1、 Blei, Felix,Fricke, Janis,Wick, Jonas,Slot, Jason C.,Hoffmeister, Dirk. "Iterative l-Tryptophan Methylation in Psilocybe Evolved by Subdomain Duplication". . p. 2160 - 2166. Retrieved 2018/10/09.