alpha-Methyl-L-tryptophan

Base Information

• Chemical Name: alpha-Methyl-L-tryptophan
• CAS No.: 16709-25-4
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• UNII: 1F33TJ4ZOP
• DSSTox Substance ID: DTXSID60350250
• Nikkaji Number: J669.716J
• Wikidata: Q82126090
• Mol file: 16709-25-4.mol

Synonyms:alpha-(11C)methyl-L-tryptophan;alpha-(14C)methyl-tryptophan;alpha-methyl-L-tryptophan;alpha-methyltryptophan;alpha-methyltryptophan, (+)-isomer;alpha-methyltryptophan, (-)-isomer;alpha-methyltryptophan, (D)-isomer;alpha-methyltryptophan, (DL)-isomer;alpha-methyltryptophan, (L)-isomer

Chemical Property of alpha-Methyl-L-tryptophan

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 1.15E-08mmHg at 25°C
• Melting Point: 168-172 °C
• Refractive Index: 1.675
• Boiling Point: 444 °C at 760 mmHg
• PKA: 2.34±0.10(Predicted)
• Flash Point: 222.3 °C
• PSA: 79.11000
• Density: 1.314 g/cm³
• LogP: 2.13100
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

≥98%, ^*data from raw suppliers

α-Methyl-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CNC2=CC=CC=C21)(C(=O)O)N
• Isomeric SMILES: C[C@](CC1=CNC2=CC=CC=C21)(C(=O)O)N
• Uses: A therapeutic and carrier molecule A therapeutic and carrier molecule.

Technology Process of alpha-Methyl-L-tryptophan

There total 19 articles about alpha-Methyl-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: 88.0%

methyl 2-(indol-3-ylmethyl)-2-aminopropionate (114524-80-0) → (S)-α-methyltryptophan (16709-25-4,13510-08-2) + α-methyl-(R)-tryptophan methyl ester (96551-27-8)

Guidance literature:

With α-chymotrypsin; In water; at 37 ℃; for 40h; Product distribution; also other α-methyl-amino acid esters investigated;

DOI:10.1016/S0040-4039(00)87608-X

Reference yield: 87.0%

(S)-N2-benzoyl-2-methyltryptophan-methylester (116139-87-8) → (S)-α-methyltryptophan (16709-25-4,13510-08-2)

Guidance literature:

With hydrogenchloride; In methanol; Heating;

DOI:10.1002/hlca.19880710124

Reference yield: 86.0%

tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate (1266681-04-2) → (S)-α-methyltryptophan (16709-25-4,13510-08-2)

Guidance literature:

tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate; With cesium hydroxide; water; In ethanol; at 70 ℃; for 4h;

With hydrogenchloride; In water;

DOI:10.1021/jo1022537

upstream raw materials:

methyl 2-(indol-3-ylmethyl)-2-aminopropionate

2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid

(S)-N²-benzoyl-2-methyltryptophan-methylester

Downstream raw materials:

L-α-methyl-tryptophan methyl ester

Refernces

• 1、 Lu, Ta-Jung,Lin, Cheng-Kun. "Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone". experimental part. p. 1621 - 1633. Retrieved 2011/06/17.
• 2、 Ekhato, I. Victor,Huang, Yun. "Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of α-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075". . p. 1019 - 1038. Retrieved 2007/10/03.