Chemical Properties
Off-white crystalline powder, soluble in methanol, slightly soluble in water, insoluble in ether, soluble in dilute acids and dilute bases, from the seeds of the legume Acacia precatorius, Chickweed Abrus fruticulosus.
Uses
1-Methyl-L-tryptophan can be used:
- In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N2-arylation of 1,2,3-triazoles.
- As a key starting material for the total synthesis of ()-ardeemin.
- In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.
Definition
ChEBI: 1-methyl-L-tryptophan is an indolyl carboxylic acid.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
The general procedure for the synthesis of acacia alkaloids from L-tryptophan and iodomethane was as follows: 10.2 g of L-tryptophan was dissolved in 130 mL of dimethylsulfoxide (DMSO), and 5 g of sodium hydroxide was added in batches over a 30-minute period under nitrogen protection. After addition, the reaction system was stirred at room temperature for 1 h. Subsequently, the reaction system was cooled to 0 °C. A 30 mL solution of DMSO with 7.46 g of iodomethane was slowly added dropwise for a controlled time of 30 minutes. After the dropwise addition, the reaction was continued for 15 hours. After completion of the reaction, 50 mL of water was added to the system to quench the reaction. The reaction mixture was poured into 400 mL of ether and a large solid was precipitated and filtered. The resulting solid was dissolved in water and the pH was adjusted to 6-7 with concentrated hydrochloric acid, and the solid was again precipitated. Filtered and dried to give 8.7 g of white powdery product (80% yield, melting point 269°C). The product was analyzed by 1H-NMR, 13C-NMR, IR spectroscopy and mass spectrometry according to standard methods. The analytical results (not shown) confirmed that the resulting solid was 1-methyltryptophan with 100% purity.
in vivo
(S)-Indoximod (5 mg/day, i.p. for 3 weeks) reverses the Bacillus Calmette-Guerin (BCG)-induced neurotoxicity in mice[3].
(S)-Indoximod (200 mg/kg, oral gavage) shows delayed, lasts longer renoprotective effect than D isomer, and increases survival in the IRI rat model[4].
(S)-Indoximod (1-9 mg/kg, i.p.) reverses cognitive, anxiety, and depressive-like behavior in bile duct ligation (BDL) rats[5].
| Animal Model: | Bile duct ligation (BDL) rats[5] |
| Dosage: | 1-9 mg/kg |
| Administration: | i.p., After the rats recovered for 7 days from BDL surgery. |
| Result: | Increased the sucrose preference.
Prevents the increased number of buried marbles.
Improved learning and memory function.
|
References
[1] Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 298 - 304
[2] Patent: CN105367477, 2016, A. Location in patent: Paragraph 0047; 0048; 0049
[3] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15021 - 15030
[4] Organic and Biomolecular Chemistry, 2006, vol. 4, # 2, p. 291 - 298
