220497-48-3

Basic information

• Product Name: (S)-N-Fmoc-3-Bromophenylalanine
• Synonyms: FMOC-3-BROMO-L-PHENYLALANINE;FMOC-L-3-BROMOPHE;FMOC-L-3-BROMOPHENYLALANINE;FMOC-PHE(3-BR)-OH;N-(9-FLUORENYLMETHOXYCARBONYL)-3-BROMOPHENYL-L-ALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-3-BROMO-L-PHENYLALANINE;(S)-N-FMOC-3-BROMOPHENYLALANINE;(S)-3-(3-BROMO-PHENYL)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PROPIONIC ACID
• CAS NO: 220497-48-3
• Molecular Formula: C₂₄H₂₀BrNO₄
• Molecular Weight: 466.32
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 220497-48-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 144.2 °C
• Boiling Point: 660.8 °C at 760 mmHg
• Flash Point: 353.4 °C
• Appearance: white powder
• Density: 1.4220 (rough estimate)
• Vapor Pressure: 2.31E-18mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Store at 0°C
• PKA: 3.70±0.10(Predicted)
• CAS DataBase Reference: (S)-N-Fmoc-3-Bromophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Fmoc-3-Bromophenylalanine(220497-48-3)
• EPA Substance Registry System: (S)-N-Fmoc-3-Bromophenylalanine(220497-48-3)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 220497-48-3(Hazardous Substances Data)

Usage

Chemical Properties

white powder

InChI:InChI=1/C24H20BrNO4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/p-1/t22-/m0/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 82311-69-1 (S)-2-amino-3-(3-bromophenyl)propanoic acid 

Relevant articles and documents

Design, synthesis, and functional assessment of Cmpd-15 derivatives as negative allosteric modulators for the β2-adrenergic receptor

The β2-adrenergic receptor (β2AR), a G protein-coupled receptor, is an important therapeutic target. We recently described Cmpd-15, the first small molecule negative allosteric modulator (NAM) for the β2AR. Herein we report in details the design, synthesis and structure-activity relationships (SAR) of seven Cmpd-15 derivatives. Furthermore, we provide in a dose-response paradigm, the details of the effects of these derivatives in modulating agonist-induced β2AR activities (G-protein-mediated cAMP production and β-arrestin recruitment to the receptor) as well as the binding affinity of an orthosteric agonist in radio-ligand competition binding assay. Our results show that some modifications, including removal of the formamide group in the para-formamido phenylalanine region and bromine in the meta-bromobenzyl methylbenzamide region caused dramatic reduction in the functional activity of Cmpd-15. These SAR results provide valuable insights into the mechanism of action of the NAM Cmpd-15 as well as the basis for future development of more potent and selective modulators for the β2AR based on the chemical scaffold of Cmpd-15.