612484-55-6

Basic information

• Product Name: BOC-7-BROMO-L-TRYPTOPHAN
• Synonyms: BOC-7-BROMO-L-TRYPTOPHAN;L-Tryptophan, 7-bromo-N-[(1,1-dimethylethoxy)carbonyl]-
• CAS NO: 612484-55-6
• Molecular Formula: C₁₆H₁₉BrN₂O₄
• Molecular Weight: 383.24
• Mol File: 612484-55-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-7-BROMO-L-TRYPTOPHAN(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-7-BROMO-L-TRYPTOPHAN(612484-55-6)
• EPA Substance Registry System: BOC-7-BROMO-L-TRYPTOPHAN(612484-55-6)

Safety Data

• Hazardous Substances Data: 612484-55-6(Hazardous Substances Data)

Usage

General Description

BOC-7-Bromo-L-tryptophan is a chemical compound that contains bromine and the amino acid tryptophan. It is commonly used in the synthesis of peptides and proteins for research purposes. BOC-7-Bromo-L-tryptophan can also be utilized as a building block for the creation of pharmaceutical drugs and bioactive molecules. Its unique structural properties make it a valuable tool for studying the interaction of proteins and other biological molecules, as well as for the development of new therapeutic agents. Additionally, its incorporation into peptide sequences can lead to altered bioactivity and improved pharmacokinetic properties, making it an important component in drug discovery and development efforts.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 75816-19-2 (S)-7-bromo-tryptophan 
• 51417-51-7 7-bromo-1H-indole 
• 34619-03-9 tert-butyldicarbonate 
• 75816-18-1 N-acetyl-7'-bromo-DL-tryptophan 
• 73-22-3 L-Tryptophan 

Downstream Products

• 612484-52-3 C₅₆H₇₆BBrN₈O₁₂ 
• 443764-18-9 2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionic acid 
• 443764-19-0 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-2-propylcarbamoyl-ethyl)-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester 
• 1289064-81-8 C₂₃H₂₅BrIN₃O₄ 

Relevant articles and documents

Suzuki–Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature

Mild reaction conditions are highly desirable for bio-orthogonal side chain derivatizations of amino acids, peptides or proteins due to the sensitivity of these substrates. Transition metal catalysed cross-couplings such as Suzuki–Miyaura reactions are highly versatile, but usually require unfavourable reaction conditions, in particular, when applied with aryl bromides. Ligand-free solvent-stabilised Pd-nanoparticles represent an efficient and sustainable alternative to conventional phosphine-based catalysts, because the cross-coupling can be performed at considerably lower temperature. We report on the application of such a highly reactive heterogeneous catalyst for the Suzuki–Miyaura cross-coupling of brominated tryptophan derivatives. The solvent-stabilised Pd-nanoparticles are even more efficient than the literature-known ADHP-Pd precatalyst. Interestingly, the latter also leads to the formation of quasi-homogeneous Pd-nanoparticles as the catalytic species. One advantage of our approach is the compatibility with aqueous and aerobic conditions at near-ambient temperatures and short reaction times of only 2 h. The influence of different Nα-protecting groups, boronic acids as well as the impact of different amino acid side chains in bromotryptophan-containing peptides has been studied. Notably, a surprising acceleration of the catalysis was observed when palladium-coordinating side chains were present in proximal positions.

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.

Synthesis of a TMC-95A Ketomethylene Analogue by Cyclization via Intramolecular Suzuki Coupling

(Equation presented) A TMC-95A analogue extended at the C-terminus with NleΨ[COCH2]Gly-Ala-Ala-NH2 was synthesized via side-chain cyclization of the linear precursor by a Suzuki cross-coupling reaction in solution to analyze the effe