203736-17-8

Basic information

• Product Name: N-Boc-5-hydroxytryptophan Methyl Ester
• Synonyms: N-Boc-5-hydroxytryptophan Methyl Ester
• CAS NO: 203736-17-8
• Molecular Formula: C₁₇H₂₂N₂O₅
• Molecular Weight: 334.36698
• Product Categories: Amino Acids & Derivatives, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 203736-17-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 555.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.262±0.06 g/cm3(Predicted)
• PKA: 10.02±0.40(Predicted)
• CAS DataBase Reference: N-Boc-5-hydroxytryptophan Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-5-hydroxytryptophan Methyl Ester(203736-17-8)
• EPA Substance Registry System: N-Boc-5-hydroxytryptophan Methyl Ester(203736-17-8)

Safety Data

• Hazardous Substances Data: 203736-17-8(Hazardous Substances Data)

Usage

Description

N-Boc-5-hydroxytryptophan Methyl Ester is a chemical compound that serves as an intermediate in the synthesis of various pharmaceuticals and bioactive molecules. It is characterized by the presence of a Boc-protecting group, a 5-hydroxytryptophan moiety, and a methyl ester functional group. N-Boc-5-hydroxytryptophan Methyl Ester plays a crucial role in the development of new therapeutic agents and drug candidates.

Uses

Used in Pharmaceutical Synthesis:
N-Boc-5-hydroxytryptophan Methyl Ester is used as an intermediate in the synthesis of 5-(2-Fluoroethoxy)-L-tryptophan (F489510), a compound with potential therapeutic applications. Its role in the synthesis process is to provide a protected and easily modifiable building block, facilitating the formation of the desired final product.
Used in Drug Development for Chagas Disease:
In the field of drug development, N-Boc-5-hydroxytryptophan Methyl Ester is utilized for the preparation of a new series of 4-Aminopyridyl-based lead inhibitors targeting Trypanosoma cruzi CYP51 (TcCYP51). This enzyme is a crucial component in the life cycle of the parasite responsible for Chagas disease, a neglected tropical disease affecting millions of people. By targeting TcCYP51, these lead inhibitors have the potential to offer novel treatment options for Chagas disease, addressing the unmet medical need for more effective therapies.

Upstream product

• 203736-19-0 (S)-2-[3-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-indol-5-yloxycarbonylamino]-3-triisopropylsilanyloxy-propionic acid benzyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 79812-02-5 2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid methyl ester 
• 4350-09-8 L-5-HTP 
• 74-88-4 methyl iodide 
• 60971-91-7 5-hydroxy-DL-tryptophan methyl ester hydrochloride 
• 67-56-1 methanol 

Downstream Products

• 203736-19-0 (S)-2-[3-((S)-2-tert-Butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-indol-5-yloxycarbonylamino]-3-triisopropylsilanyloxy-propionic acid benzyl ester 
• 1219197-92-8 (S)-3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid 

Relevant articles and documents

NOVEL AGENTS TARGETING CYP51

The invention provides inhibitors of a sterol C14-demethylase, a new series of 4- aminopyridyl-based lead inhibitors targeting Trypanosoma cruzi CYP51 (TcCYP51) developed using structure-based drug design as well as structure -property relationship (SPR)

An enantioselective recyclable polystyrene-supported threonine-derived organocatalyst for aldol reactions

A series of primary amino acids covalently supported onto polystyrene through alkyne-azide cycloaddition reactions has been synthesized and evaluated as catalysts in asymmetric aldol reactions. A polymer-supported threonine behaves as an easily recyclable, highly reactive and stereoselective (up to 99% ee) catalyst in the aldol reaction of both cyclic and acyclic ketone donors with aromatic aldehydes in aqueous environments. While cyclic ketones react with anti diastereoselectivity, syn adducts are predominantly obtained with acyclic substrates. The heterogenized threonine catalyst has been used for the sequential synthesis of a small library of enantiopure aldol products.

Building addressable libraries: Amino acid derived fluorescent linkers

A new amino acid derived fluorescent linker for attaching molecules to the surface of a microelectrode array has been developed. Molecules to be monitored on an array are attached to the C-terminus of the linker, the N-terminus is then used to attach the linker to the array, and the side chain is used to synthesize a fluorescent tag. The fluorescent group is made with a one-step oxidative cycloaddition reaction starting from a hydroxyindole group. The linker is compatible with site-selective Cu(I)-chemistry on the array, it allows for quality control assessment of the array itself, and it is compatible with the electrochemical impedance experiments used to monitor binding events on the surface of the array.