199110-64-0

Basic information

• Product Name: FMOC-L-4,4'-BIPHENYLALANINE
• Synonyms: (S)-3-BIPHENYL-4-YL-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PROPIONIC ACID;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-4,4'-BIPHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-BIPHENYLALANINE;FMOC-4-BIPHENYL-L-ALA;FMOC-4-PHENYL-PHE-OH;FMOC-4-PHENYL-PHENYLALANINE;FMOC-BETA-(4-BIPHENYLYL)-ALA-OH;FMOC-BIP-OH
• CAS NO: 199110-64-0
• Molecular Formula: C₃₀H₂₅NO₄
• Molecular Weight: 463.52
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 199110-64-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 700.7 °C at 760 mmHg
• Flash Point: 377.6 °C
• Appearance: /
• Density: 1.257±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.13E-27mmHg at 25°C
• Refractive Index: 1.651
• Storage Temp.: 2-8°C
• PKA: 3.77±0.10(Predicted)
• CAS DataBase Reference: FMOC-L-4,4'-BIPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-4,4'-BIPHENYLALANINE(199110-64-0)
• EPA Substance Registry System: FMOC-L-4,4'-BIPHENYLALANINE(199110-64-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 199110-64-0(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Fmoc-l-4,4''-biphenylalanine

InChI:InChI=1/C33H30N2O6/c34-29(31(36)37)17-20-9-13-22(14-10-20)23-15-11-21(12-16-23)18-30(32(38)39)35-33(40)41-19-28-26-7-3-1-5-24(26)25-6-2-4-8-27(25)28/h1-16,28-30H,17-19,34H2,(H,35,40)(H,36,37)(H,38,39)/t29-,30-/m0/s1

Upstream product

• 198561-04-5 Fmoc-4-bromo-L-phenylalanine 
• 98-80-6 phenylboronic acid 
• 82311-69-1 (S)-2-amino-3-(3-bromophenyl)propanoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 164172-95-6 (S)-3-([1,1'-biphenyl]-3-yl)-2-aminopropanoic acid 
• 24250-84-8 H-p-BrPhe-OH 

Downstream Products

• 1275576-52-7 C₂₅H₂₆N₂O₄ 
• 155760-02-4 (S)-3-([1,1'-biphenyl]-4-yl)-2-aminopropanoic acid 
• 611209-96-2 N-(9-fluorenylmethoxycarbonyl)-L-biphenylalaninol 

Relevant articles and documents

Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions

A one-step synthesis of Fmoc-protected aryl/heteroaryl-substituted phenylalanines (Bip derivatives) using the nonaqueous palladium-catalyzed Suzuki-Miyaura cross-coupling (SMC) reaction of Fmoc-protected bromo- or iodophenylalanines is reported. This protocol allows for the direct formation of a variety of unnatural biaryl-containing amino acids in good to excellent yield, which can be readily used in subsequent Fmoc solid-phase peptide synthesis. The synthetic utility of this method is also demonstrated by the SMC reaction of bromophenylalanine-containing tripeptides.

Drug Design Inspired by Nature: Crystallographic Detection of an Auto-Tailored Protease Inhibitor Template

De novo drug discovery is still a challenge in the search for potent and selective modulators of therapeutically relevant target proteins. Here, we disclose the unexpected discovery of a peptidic ligand 1 by X-ray crystallography, which was auto-tailored by the therapeutic target MMP-13 through partial self-degradation and subsequent structure-based optimization to a highly potent and selective β-sheet peptidomimetic inhibitor derived from the endogenous tissue inhibitors of metalloproteinases (TIMPs). The incorporation of non-proteinogenic amino acids in combination with a cyclization strategy proved to be key for the de novo design of TIMP peptidomimetics. The optimized cyclic peptide 4 (ZHAWOC7726) is membrane permeable with an IC50 of 21 nm for MMP-13 and an attractive selectivity profile with respect to a polypharmacology approach including the anticancer targets MMP-2 (IC50: 170 nm) and MMP-9 (IC50: 140 nm).