50517-10-7

Usage

Chemical Properties

White Solid

Uses

A derivative of 6-Chlorotryptophan

Upstream product

• 17422-33-2 6-chloroindole 
• 56-45-1 L-serin 
• 108-24-7 acetic anhydride 
• 302-84-1 serin 

Downstream Products

• 56777-76-5 N^α-acetyl-6-chloro-D-tryptophan 
• 59767-02-1 N^α-acetyl-6-chloro-L-tryptophan 
• 56632-86-1 D-6-chlorotryptophan 
• 33468-35-8 6-chloro-DL-tryptophan 
• 1034402-47-5 6-chloro-N_α-acetyltryptophan methyl ester 
• 908847-42-7 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(6-chloro-1H-indol-3-yl)propanoic acid 

Relevant academic research and scientific papers

A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan

A metal-free 2-selenylation of tryptophan derivatives is reported, where the use of iodide as the catalyst and oxone as the oxidant is key to obtain high yields. Various functional groups within the di-seleny and the indole ring are tolerated, and no racemization is generally observed.

MACROCYCLIC PEPTIDOMIMETICS FOR ALPHA-HELIX MIMICRY

Methods and compositions are provided for generating macrocyclic peptides constrained by side-chain-to-C-terminus non-peptidic tethers for use as functional and structural mimics of α-helical motifs, including in therapeutic applications. These methods can be used to produce libraries of conformationally constrained peptidomimetics to identify compounds with desired activity properties.

Synthesis of tripeptides containing d-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception

The noncationizable tripeptide Ac-d-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of d-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.

Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against ID

The facile synthesis of a series of tryptophan derivatives

This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.