75816-20-5

Usage

Uses

Used in Medicinal Chemistry:
BOC-5-Bromo-L-tryptophan is used as a synthetic building block for the creation of peptide and protein derivatives, facilitating the development of novel bioactive compounds with potential therapeutic applications.
Used in Drug Discovery:
BOC-5-BROMO-L-TRYPTOPHAN is utilized as a precursor in the synthesis of new pharmaceuticals, particularly those targeting specific biological interactions, due to its unique structural features and reactivity.
Used in Research and Development of Peptide-Based Pharmaceuticals:
BOC-5-Bromo-L-tryptophan is employed as a key component in the design and synthesis of peptide-based drugs, contributing to the advancement of targeted therapies and precision medicine.
Used in Investigation of Enzyme-Substrate Interactions:
The presence of the 5-bromo group in BOC-5-Bromo-L-tryptophan allows for its use in studying the mechanisms of enzyme action and substrate specificity, providing insights into enzyme function and regulation.
Used in Investigation of Protein-Protein Interactions:
BOC-5-BROMO-L-TRYPTOPHAN is applied in research aimed at understanding the complex networks of protein interactions, which is crucial for elucidating the molecular basis of various biological processes and diseases.

Upstream product

• 75816-15-8 N^α-acetyl-5-bromo-D,L-tryptophan 
• 24424-99-5 di-tert-butyl dicarbonate 
• 6548-09-0 5-bromo-DL-tryptophan 
• 75816-19-2 (S)-7-bromo-tryptophan 

Relevant academic research and scientific papers

Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo

Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with 18F and their biological evaluation. 4-7-[18F]Fluorotryptophans ([18F]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7-[18F]FTrps in different tumor cell lines. 4, 5-, and 6-[18F]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[18F]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[18F]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[18F]FTrp represents a highly promising PET probe for imaging of Trp metabolism.

Mild, Aqueous α-Arylation of Ketones: Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules

The palladium-catalysed aqueous α-arylation of ketones was developed and tested for a large variety of reaction partners. These mild conditions enabled the coupling of aryl/alkyl-ketones with N-protected halotryptophans, heterocyclic haloarenes, and challenging base-sensitive compounds. The synthetic potential of this new methodology for the diversification of complex bioactive molecules was exemplified by derivatising prochlorperazine. The methodology is mild, aqueous and flexible, representing a means of functionalizing a wide range of halo-aromatics and therefore has the potential to be extended to complex molecule diversification.

Somatostatin analogs having a substituted tryptophyl residue in position eight

Tetradecapeptides of the formula STR1 in which A represents L, D or DL 5- or 6- fluoro-, bromo-,chloro- or iodotryptophyl, or a therapeutically acceptable acid addition salt thereof, their preparation and intermediates for their preparation are disclosed. The tetradecapeptides are useful for inhibiting the release of growth hormone. Compositions and methods for their use also are disclosed.