114873-17-5

Basic information

• Product Name: BOC-5-BROMO-D-TRYPTOPHAN
• Synonyms: BOC-5-BROMO-D-TRYPTOPHAN;D-Tryptophan, 5-bromo-N-[(1,1-dimethylethoxy)carbonyl]-;Boc-D-5-BromoTryptophan
• CAS NO: 114873-17-5
• Molecular Formula: C16H19BrN2O4
• Molecular Weight: 383.24
• Mol File: 114873-17-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-5-BROMO-D-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-5-BROMO-D-TRYPTOPHAN(114873-17-5)
• EPA Substance Registry System: BOC-5-BROMO-D-TRYPTOPHAN(114873-17-5)

Safety Data

• Hazardous Substances Data: 114873-17-5(Hazardous Substances Data)

Usage

General Description

BOC-5-Bromo-D-tryptophan is a chemical compound belonging to the class of tryptophan derivatives. It is a derivative of the essential amino acid tryptophan, with a bromine atom attached to the 5-position of the indole ring and a BOC (tert-butyloxycarbonyl) protecting group attached to the amino group. BOC-5-BROMO-D-TRYPTOPHAN is primarily used in the synthesis of peptides and proteins, as well as in pharmaceutical research and development. Its unique structure and properties make it a valuable tool in the field of medicinal chemistry and drug discovery. BOC-5-Bromo-D-tryptophan has potential applications in the development of new pharmaceuticals and bioactive compounds due to its ability to modulate protein-protein interactions and its potential as a building block for the synthesis of novel peptides with therapeutic potential.

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 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 6548-09-0 5-bromo-DL-tryptophan 
• 133766-35-5 ethyl 2-hydroximino-3-(5-bromoindol-3-yl)propanoate 
• 10075-50-0 5-bromo-1H-indole 
• 133766-37-7 N-Boc-5-bromo-DL-tryptophan ethyl ester 

Downstream Products

• 103343-28-8 3-(5-Bromo-1H-indol-3-ylmethyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 

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.

Preparation and evaluation of L- and D-5-[18F]fluorotryptophan as PET imaging probes for indoleamine and tryptophan 2,3-dioxygenases

Indoleamine and tryptophan 2,3-dioxygenases (IDO1 and TDO2) are pyrrolases catalyzing the oxidative cleavage of the 2,3-double bond of L-tryptophan in kynurenine pathway. In the tumor microenvironment, their increased activity prevents normal immune function, i.e. tumor cell recognition and elimination by cytotoxic T-cells. Consequently, inhibition of the kynurenine pathway may enhance the activity of cancer immunotherapeutics by reversing immune dysfunction. We sought to investigate the properties of radiolabeled 5-[18F]fluorotryptophan with respect to its ability for measuring IDO1 and TDO2 activity by positron emission tomography (PET). Results L-5-[18F]fluorotryptophan and D-5-[18F]fluorotryptophan were synthesized by Cu(I) catalyzed [18F]fluorodeboronylation of Boc/tBu protected precursors in moderate yields (1.5?±?0.6%) sufficient for pre-clinical studies. The specific activity of the product was 407–740?GBq/μmol, radiochemical purity >99% and enantiomeric excess 90–99%. Enzymatic assay confirmed that L-5-fluorotryptophan is an IDO1 and TDO2 substrate whereas the D-isomer is not. In-vitro cell uptake experiments using CT26 cells with doxycycline-induced overexpression of human-IDO1 and human-TDO2 revealed an elevated cell uptake of L-5-[18F]fluorotryptophan upon induction of IDO1 or TDO2 enzymes compared to baseline; however, the uptake was observed only in the presence of low L-tryptophan levels in media. PET imaging experiments performed using tumor bearing mouse models expressing IDO1 at various levels (CT26, CT26-hIDO1, 17082A, 17095A) showed tumor uptake of the tracer elevated up to 8%ID/g; however, the observed tumor uptake could not be attributed to IDO1 activity in the tumor tissue. The metabolism of L- and D- isomers was markedly different in vivo, the D-isomer was excreted by a combination of hepatobiliary and renal routes, the L-isomer underwent extensive metabolism to [18F]fluoride. Conclusion The observed in vivo tumor uptake of the tracer could not be attributed to IDO1 or TDO2 enzyme activity in the tumor, presumably due to competition with endogenous tryptophan as well as rapid tracer 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.