1234880-33-1

Basic information

• Product Name: (R)-N-Boc-5-Hydroxy-Trp-OMe
• Synonyms: (R)-N-Boc-5-Hydroxy-Trp-OMe;-3-(5-hydroxy-1H-indol-3-yl);-Methyl 2-((tert-butoxycarbonyl)
• CAS NO: 1234880-33-1
• Molecular Formula: C17H22N2O5
• Molecular Weight: 334.36698
• Mol File: 1234880-33-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (R)-N-Boc-5-Hydroxy-Trp-OMe(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Boc-5-Hydroxy-Trp-OMe(1234880-33-1)
• EPA Substance Registry System: (R)-N-Boc-5-Hydroxy-Trp-OMe(1234880-33-1)

Safety Data

• Hazardous Substances Data: 1234880-33-1(Hazardous Substances Data)

Usage

Description

(R)-N-Boc-5-Hydroxy-Trp-OMe, also known as N-alpha-boc-5-hydroxy-L-tryptophan methyl ester, is a chemical compound belonging to the class of tryptophan derivatives. It is a derivative of 5-hydroxytryptophan, an intermediate in the biosynthesis of serotonin. (R)-N-Boc-5-Hydroxy-Trp-OMe is characterized by its Boc-protected amino group and methyl ester functional groups, making it suitable for various synthetic routes. Its specific properties and potential applications make it an important compound for the development of new drugs and chemical compounds with therapeutic potential.

Uses

Used in Organic Chemistry:
(R)-N-Boc-5-Hydroxy-Trp-OMe is used as a starting material for the synthesis of biologically active molecules and pharmaceuticals. Its Boc-protected amino group and methyl ester functional groups allow for versatile synthetic routes, making it a valuable compound in the field of organic chemistry.
Used in Drug Research:
In the pharmaceutical industry, (R)-N-Boc-5-Hydroxy-Trp-OMe is used as a key intermediate in the development of new drugs with therapeutic potential. Its unique structure and functional groups enable the creation of novel drug candidates that can target various medical conditions.
Used in the Synthesis of Serotonin-Related Compounds:
Given its structural similarity to 5-hydroxytryptophan, an intermediate in the biosynthesis of serotonin, (R)-N-Boc-5-Hydroxy-Trp-OMe can be used in the synthesis of compounds related to serotonin. This makes it a valuable tool in the study and development of treatments for conditions related to serotonin imbalances, such as depression and anxiety.
Used in the Development of Serotonin Receptor Agonists and Antagonists:
Due to its structural relationship with serotonin, (R)-N-Boc-5-Hydroxy-Trp-OMe can be employed in the development of serotonin receptor agonists and antagonists. These compounds can be used to modulate the activity of serotonin receptors, potentially leading to new treatments for a variety of conditions, including mood disorders, migraines, and other neurological diseases.

Upstream product

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

Downstream Products

• 1219197-92-8 (S)-3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid 

Relevant articles and documents

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.

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)

Rational development of 4-aminopyridyl-based inhibitors targeting trypanosoma cruzi CYP51 as anti-chagas agents

A new series of 4-aminopyridyl-based lead inhibitors targeting Trypanosoma cruzi CYP51 (TcCYP51) has been developed using structure-based drug design as well as structure-property relationship (SPR) analyses. The screening hit starting point, LP10 (KD ≤ 42 nM; EC50 = 0.65 μM), has been optimized to give the potential leads 14t, 27i, 27q, 27r, and 27t, which have low-nanomolar binding affinity to TcCYP51 and significant activity against T. cruzi amastigotes cultured in human myoblasts (EC50 = 14-18 nM for 27i and 27r). Many of the optimized compounds have improved microsome stability, and most are selective against human CYPs 1A2, 2D6, and 3A4 (50% inhibition at 1 μM). A rationale for the improvement in microsome stability and selectivity of inhibitors against human metabolic CYP enzymes is presented. In addition, the binding mode of 14t with the Trypanosoma brucei CYP51 (TbCYP51) orthologue has been characterized by X-ray structure analysis.