908847-42-7

Basic information

• Product Name: Fmoc-6-chloro L-Tryptophan
• Synonyms: Fmoc-6-chloro L-Tryptophan;6-Chloro-N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-tryptophan;FMoc-6-chloro (S)-Tryptophan;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-(6-chloro-1H-indol-3-yl)propanoic acid;6-Chloro-N-Fmoc-L-tryptophan;Fmoc-Trp(6-Cl)-OH;Fmoc-6-chloro-L-tryptophane;L-Tryptophan, 6-chloro-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-
• CAS NO: 908847-42-7
• Molecular Formula: C26H21ClN2O4
• Molecular Weight: 460.90894
• Product Categories: Amino Acids & Derivatives;Chiral Reagents;Heterocycles
• Mol File: 908847-42-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 732.617°C at 760 mmHg
• Flash Point: 396.872°C
• Appearance: /
• Density: 1.406g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.72±0.10(Predicted)
• CAS DataBase Reference: Fmoc-6-chloro L-Tryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-6-chloro L-Tryptophan(908847-42-7)
• EPA Substance Registry System: Fmoc-6-chloro L-Tryptophan(908847-42-7)

Safety Data

• Hazardous Substances Data: 908847-42-7(Hazardous Substances Data)

Usage

Uses

Fmoc-6-chloro L-Tryptophan is used for preparation of acyltryptophanols as FSH antagonists.

InChI:InChI=1/C26H21ClN2O4/c27-16-9-10-17-15(13-28-23(17)12-16)11-24(25(30)31)29-26(32)33-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22,24,28H,11,14H2,(H,29,32)(H,30,31)/t24-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 50517-10-7 N^α-acetyl-6-chloro-D,L-tryptophan 
• 17422-33-2 6-chloroindole 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 33468-35-8 6-chloro-DL-tryptophan 

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.

PEPTIDOMIMETIC MACROCYCLES AND USES THEREOF

The present disclosure describes methods of using peptidomimetic macrocycles in combination with an additional therapy to treat a condition, for example, cancer. In some embodiments, the peptidomimetic macrocycle can mitigate a side effect (e.g., mucositis, neutropenia, or thrombocytopenia) of the additional therapy.

Synthesis of cell-permeable stapled peptide dual inhibitors of the p53-Mdm2/Mdmx interactions via photoinduced cycloaddition

We report the first application of a photoinduced 1,3-dipolar cycloaddition reaction to 'staple' a peptide dual inhibitor of the p53-Mdm2/Mdmx interactions. A series of stapled peptide inhibitors were efficiently synthesized and showed excellent dual inhi