Description

n-Fmoc-(2R,3R)-3-Amino-2-Hydroxy-3-(3-Trifluoromethyl-Phenyl)-Propionic Acid is a sophisticated, non-natural amino acid derivative featuring a stereochemically defined β-hydroxy-α-amino acid scaffold with a trifluoromethylphenyl side chain. This compound is a critical chiral building block for the synthesis of complex peptides and peptidomimetics, where its structural features can impart enhanced metabolic stability, binding affinity, and membrane permeability. It is primarily utilized by research institutions and pharmaceutical companies engaged in the development of novel therapeutic agents, including protease inhibitors and bioactive peptide libraries.

Application

• Solid-Phase Peptide Synthesis (SPPS): As an Fmoc-protected amino acid, it is a key monomer for the automated synthesis of peptides containing non-proteinogenic residues.
• Peptidomimetic Drug Discovery: Serves as a core scaffold for designing and constructing peptidomimetics with improved pharmacological profiles, leveraging the trifluoromethyl group for enhanced lipophilicity and bioavailability.
• Protease Inhibitor Development: The β-hydroxy-α-amino acid structure is a common motif in inhibitors of aspartyl proteases (e.g., renin, HIV protease) and other enzyme classes.
• Chemical Biology Probes: Used to incorporate stable, fluorinated tags into peptides for studies using 19F NMR or to modulate peptide-protein interactions.
• Pharmaceutical Intermediate: An advanced intermediate in the multi-step synthesis of targeted active pharmaceutical ingredients (APIs) for preclinical and clinical research.
• Chiral Pool Synthesis: Provides a source of defined chirality for the asymmetric synthesis of more complex organic molecules beyond peptides.

Basic Information

Product Name	n-Fmoc-(2R,3R)-3-Amino-2-Hydroxy-3-(3-Trifluoromethyl-Phenyl)-Propionic Acid
CAS No.	1217817-77-0
Molecular Formula	C26H22F3NO5
Molecular Weight	485.45 g/mol
Synonyms	Fmoc-(2R,3R)-3-Amino-2-hydroxy-3-[3-(trifluoromethyl)phenyl]propanoic Acid; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-amino-2-hydroxy-3-(3-trifluoromethylphenyl)propionic acid (2R,3R)-isomer; (2R,3R)-2-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxy-3-[3-(trifluoromethyl)phenyl]propanoic Acid; Fmoc-Thr(3-CF3Ph)-OH (stereospecific); (2R,3R)-N-Fmoc-3-Amino-2-hydroxy-3-(3-trifluoromethylphenyl)propionic Acid; Fmoc-β3-hThr(3-CF3Ph)-OH; Fmoc-protected β-Hydroxy-α-amino acid derivative
EINECS	Contact for details

Quality Control

Our production of n-Fmoc-(2R,3R)-3-Amino-2-Hydroxy-3-(3-Trifluoromethyl-Phenyl)-Propionic Acid adheres to stringent quality protocols to ensure batch-to-batch consistency and high chemical purity, essential for sensitive pharmaceutical research. Each lot is characterized by advanced analytical techniques including HPLC, NMR, and mass spectrometry. Certificates of Analysis (COA) detailing purity, chiral purity, and impurity profiles are provided and can be tailored to meet specific client requirements or internal quality standards.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at 2-8°C or as specified on the label or COA. This product is hygroscopic (moisture-sensitive) and should be handled under anhydrous conditions to maintain stability and purity. Allow the container to reach room temperature before opening to prevent condensation.

Specification

Item	Specification
Appearance	White to off-white powder
Identification (IR)	Conforms to structure
Identification (NMR)	Conforms to structure
Assay (HPLC)	≥ 97.0%
Chiral Purity (Chiral HPLC)	≥ 99.0% de (2R,3R)
Water Content (KF)	≤ 1.0%
Heavy Metals	≤ 20 ppm
Residual Solvents (GC)	Complies with ICH guidelines

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.