1079926-36-5

Basic information

• Product Name: 5-(4-methoxyphenyl)-L-tryptophan
• Synonyms: 5-(4-methoxyphenyl)-L-tryptophan
• CAS NO: 1079926-36-5
• Molecular Weight: 310.353
• Mol File: 1079926-36-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-(4-methoxyphenyl)-L-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-methoxyphenyl)-L-tryptophan(1079926-36-5)
• EPA Substance Registry System: 5-(4-methoxyphenyl)-L-tryptophan(1079926-36-5)

Safety Data

• Hazardous Substances Data: 1079926-36-5(Hazardous Substances Data)

Upstream product

• 139684-34-7 5-bromo-L-tryptophan hydrochloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 73-22-3 L-Tryptophan 
• 6548-09-0 5-bromo-DL-tryptophan 

Relevant articles and documents

Modular Combination of Enzymatic Halogenation of Tryptophan with Suzuki-Miyaura Cross-Coupling Reactions

The combination of the biocatalytic halogenation of l-tryptophan with subsequent chemocatalytic Suzuki-Miyaura cross-coupling reactions leads to the modular synthesis of an array of C5, C6, or C7 aryl-substituted tryptophan derivatives. In a three-step one-pot reaction, the bromo substituent is initially incorporated regioselectively by immobilized tryptophan 5-, 6-, or 7-halogenases, respectively, with concomitant cofactor regeneration. The halogenation proceeds in aqueous media at room temperature in the presence of NaBr and O2. After the separation of the biocatalyst by filtration, a Pd catalyst, base, and boronic acid are added to the aryl halide formed in situ to effect direct Suzuki-Miyaura cross-coupling reactions followed by tert-butoxycarbonyl (Boc) protection. After a single purification step, different Boc-protected aryl tryptophan derivatives are obtained that can, for example, be used for peptide or peptidomimetic synthesis. Putting the pieces together: By combining the enzymatic halogenation of l-tryptophan using flavin adenine dinucleotide dependent halogenases with Pd-catalyzed Suzuki-Miyaura cross-coupling reactions in water, the C5-, C6-, or C7-position of the indole ring can be brominated regioselectively in situ and functionalized chemocatalytically in a stepwise one-pot reaction.