75816-20-5

Basic information

• Product Name: BOC-5-BROMO-L-TRYPTOPHAN
• Synonyms: BOC-5-BROMO-L-TRYPTOPHAN;L-Tryptophan, 5-bromo-N-[(1,1-dimethylethoxy)carbonyl]-;Boc-L-5-BromoTryptophan
• CAS NO: 75816-20-5
• Molecular Formula: C₁₆H₁₉BrN₂O₄
• Molecular Weight: 383.24
• Mol File: 75816-20-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-5-BROMO-L-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-5-BROMO-L-TRYPTOPHAN(75816-20-5)
• EPA Substance Registry System: BOC-5-BROMO-L-TRYPTOPHAN(75816-20-5)

Safety Data

• Hazardous Substances Data: 75816-20-5(Hazardous Substances Data)

Usage

General Description

BOC-5-Bromo-L-tryptophan is a derivative of the amino acid tryptophan with a protective BOC (tert-butyloxycarbonyl) group attached. It is commonly used as a building block in the synthesis of peptide and protein derivatives. The presence of the 5-bromo group makes this compound useful for binding studies and as a precursor for the synthesis of bioactive compounds. BOC-5-Bromo-L-tryptophan has potential applications in medicinal chemistry, drug discovery, and other research areas related to the development of peptide-based pharmaceuticals. Additionally, it may also have utility in the investigation of enzyme-substrate interactions and protein-protein interactions.

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 articles and documents

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.

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.