1257849-07-2

Basic information

• Product Name: Fmoc-5-chloro-L-tryptophan
• Synonyms: Fmoc-5-chloro-L-tryptophan;Fmoc-Trp(5-Cl)-OH;5-Chloro-N-Fmoc-L-tryptophan;(9H-Fluoren-9-yl)MethOxy]Carbonyl Trp(5-Cl)-OH;Fmoc-L-5-ChloroTryptophan
• CAS NO: 1257849-07-2
• Molecular Formula: C26H21ClN2O4
• Molecular Weight: 460.90894
• Mol File: 1257849-07-2.mol

Chemical Properties

• Boiling Point: 732.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.406±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.71±0.10(Predicted)
• CAS DataBase Reference: Fmoc-5-chloro-L-tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-5-chloro-L-tryptophan(1257849-07-2)
• EPA Substance Registry System: Fmoc-5-chloro-L-tryptophan(1257849-07-2)

Safety Data

• Hazardous Substances Data: 1257849-07-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-5-chloro-L-tryptophan is used as a building block for the synthesis of peptide-based drugs, leveraging its ability to selectively react with other amino acids to form peptide bonds. This selective reactivity is crucial for the precise construction of complex peptide structures, which are vital for the development of novel therapeutic agents.
Used in Biotechnology Industry:
In the biotechnology field, Fmoc-5-chloro-L-tryptophan serves as a key component in the creation of recombinant proteins and other bioactive peptides. Its role in solid-phase peptide synthesis allows for the efficient production of proteins with specific functionalities, which are essential for research and various biotechnological applications.
Used in Research and Development:
Fmoc-5-chloro-L-tryptophan is utilized as a research tool for studying the properties and interactions of peptides and proteins. Its unique structural features enable scientists to investigate the effects of specific amino acid substitutions on protein function and stability, contributing to a deeper understanding of peptide and protein behavior.

Upstream product

• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 17422-32-1 5-chloro-1H-indole 

Relevant articles and documents

Structure-Based Design of Melanocortin 4 Receptor Ligands Based on the SHU-9119-hMC4R Cocrystal Structure ?

The melanocortin receptors (MC1R-MC5R) belong to class A G-protein-coupled receptors (GPCRs) and are known to have receptor-specific roles in normal and diseased states. Selectivity for MC4R is of particular interest due to its involvement in various metabolic disorders, including obesity, feeding regulation, and sexual dysfunctions. To further improve the potency and selectivity of MC4R (ant)agonist peptide ligands, we designed and synthesized a series of cyclic peptides based on the recent crystal structure of MC4R in complex with the well-characterized antagonist SHU-9119 (Ac-Nle4-c[Asp5-His6-DNal(2′)7-Arg8-Trp9-Lys10]-NH2). These analogues were pharmacologically characterized in vitro, giving key insights into exploiting binding site subpockets to deliver more selective ligands. More specifically, the side chains of the Nle4, DNal(2′)7, and Trp9 residues in SHU-9119, as well as the amide linkage between the Asp5 and Lys10 side chains, were found to represent structural features engaging a hMC4R/hMC3R selectivity switch.

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.