25198-03-2

Basic information

• Product Name: 7-Methoxy-L-tryptophan
• Synonyms: 7-Methoxy-L-tryptophan;L-Tryptophan, 7-methoxy-
• CAS NO: 25198-03-2
• Molecular Formula: C12H14N2O3
• Molecular Weight: 234.25116
• EINECS: -0
• Mol File: 25198-03-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Methoxy-L-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methoxy-L-tryptophan(25198-03-2)
• EPA Substance Registry System: 7-Methoxy-L-tryptophan(25198-03-2)

Safety Data

• Hazardous Substances Data: 25198-03-2(Hazardous Substances Data)

Usage

Uses

7-Methoxy-L-Tryptophan is a derivative of L-Tryptophan (T947210), an essential amino acid.

Upstream product

• 220906-11-6 (2R,5S)-3,6-diethoxy-2-isopropyl-5-[3-(triethylsilyl)prop-2-ynyl]-2,5-dihydropyrazine 
• 354574-31-5 2-iodo-6-methoxybenzenamine 

Relevant articles and documents

General approach for the synthesis of 12-methoxy-substituted sarpagine indole alkaloids including (-)-12-methoxy-Nb-methylvoachalotine, (+)-12-methoxy-Na-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline

The enantiospecific synthesis of 7-methoxy-D-tryptophan ethyl ester was completed by combination of the Larock heteroannulation process with a Schoellkopf-based chiral auxiliary in good yield. This ester was then employed in the first regiospecific, stere

Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution

Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with p = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.