Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
【 Providing a complete set of intermediates and impurities for L ifitegrast 】
【 Providing a complete set of intermediates and impurities for L ifitegrast 】
【 Providing a complete set of intermediates and impurities for L ifitegrast 】
Here is a detailed product description for CAS 1289646-76-9: (S)-2-((tert-Butoxycarbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoic acid :
1. Chemical Identification: * CAS Number: 1289646-76-9 * IUPAC Name: (2S)-2-[(tert-butoxycarbonyl)amino]-3-[3-(methylsulfonyl)phenyl]propanoic acid * Synonyms: * (S)-2-(Boc-amino)-3-(3-(methylsulfonyl)phenyl)propionic acid * Boc-(S)-3-(3-(methylsulfonyl)phenyl)alanine * Boc-3-(3-(Methylsulfonyl)phenyl)-L-alanine * N-Boc-3-(3-(Methylsulfonyl)phenyl)-L-alanine * Molecular Formula: C₁₅H₂₁NO₆S * Molecular Weight: 343.39 g/mol
2. Structural Features: * Core Structure: Derived from the natural amino acid L-Alanine ( (S)-2-aminopropanoic acid ). * Protecting Group: Contains a tert-Butoxycarbonyl (Boc) group on the alpha-amino (-NH₂) group. This group: * Temporarily masks the amino group's reactivity. * Is stable to many reaction conditions but readily removed under acidic conditions (e.g., TFA, HCl). * Crucial for stepwise peptide synthesis. * Side Chain: The alanine beta-carbon is substituted with a 3-(methylsulfonyl)phenyl group. * Contains a phenyl ring (aromatic). * Has a strong methylsulfonyl (-SO₂CH₃) electron-withdrawing group at the meta (3-) position relative to the attachment point to the alanine chain. This group enhances stability, polarity, and can participate in specific binding interactions (e.g., hydrogen bonding acceptor). * Chirality: The alpha-carbon (adjacent to the carboxylic acid and Boc-amino group) is chiral and specifically in the (S)-configuration . This corresponds to the natural L-stereochemistry . * Carboxylic Acid: The terminal α-carboxylic acid group is typically free and unprotected, allowing for coupling reactions in peptide synthesis.
3. Physical Properties (Typical): * Physical State: Solid (commonly a white to off-white powder or crystalline solid). * Solubility: * Soluble in polar organic solvents (e.g., Dimethylformamide (DMF), Dimethyl Sulfoxide (DMSO), Dichloromethane (DCM), Methanol, Ethanol, Acetonitrile). * Less soluble or insoluble in non-polar solvents (e.g., Hexanes, Toluene). * Very low solubility in water due to the hydrophobic Boc group and aromatic ring. * Melting Point: Specific values vary but typically high (>100°C, often reported around 140-160°C range; exact value depends on purity and crystallization conditions). * Optical Rotation: Exhibits a specific optical rotation ([α]D) due to its chiral center. The exact value is characteristic for identification/purity but depends on solvent and concentration. Literature reports values around +15° to +25° (c=1, DMF or MeOH) are common. * Spectroscopic Data: Characterized by NMR (¹H, ¹³C), LC-MS (HPLC-MS), IR, and elemental analysis for identity and purity confirmation. Key features include Boc methyl signals (~1.4 ppm NMR), aromatic protons (7.5-8.1 ppm NMR), sulfonyl group IR stretch (~1300-1350 cm⁻¹ SO₂ asym, ~1140-1160 cm⁻¹ SO₂ sym), and carboxylic acid IR stretch (~1700-1725 cm⁻¹).
4. Primary Applications: * Peptide Synthesis: This compound is a specialized, non-canonical amino acid building block used in solid-phase peptide synthesis (SPPS) or solution-phase peptide synthesis. The Boc group protects the amine during coupling steps. Its primary role is to introduce the unique 3-(methylsulfonyl)phenylalanine residue with L-stereochemistry into the peptide chain. * Pharmaceutical Research & Drug Discovery: The inclusion of the meta-methylsulfonylphenyl group is significant because: * The sulfonyl group (-SO₂-) is a common pharmacophore found in many bioactive molecules and drugs. * It acts as a strong hydrogen bond acceptor, potentially enhancing binding affinity to target proteins. * It increases polarity and metabolic stability compared to simpler phenylalanine analogs. * It can modulate the electronic properties and conformation of the peptide/protein it's incorporated into. * Used to study structure-activity relationships (SAR), develop enzyme inhibitors, receptor ligands, or therapeutic peptides targeting specific diseases. * Chemical Biology: Used as a probe to study protein-protein interactions, enzyme mechanisms, or to create peptides with tailored physicochemical properties.
5. Handling and Storage: * Storage: Store at 2-8°C (refrigerated) under an inert atmosphere (e.g., nitrogen or argon) to maximize shelf life and stability. Protect from moisture and humidity as the Boc group can be sensitive to prolonged exposure. Long-term storage may require freezing (-15°C to -25°C). * Stability: Stable under normal laboratory conditions when stored properly. Sensitive to strong acids (removes Boc group), strong bases (hydrolysis), and prolonged exposure to moisture/heat. * Handling: Handle with standard laboratory precautions. Use in a well-ventilated area (fume hood). Wear appropriate personal protective equipment (PPE): lab coat, gloves (nitrile recommended), and safety glasses. Avoid inhalation of dust and contact with skin or eyes. Not known to be highly toxic, but treat as a potential irritant.
