Chemical Identity and Structural Features

(S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride is a protected non-natural amino acid derivative built on a phenylalanine scaffold. The compound bears three key structural elements: (1) an S-configured α-amino group presented as its hydrochloride salt, ensuring protonation and enhanced solid-state stability; (2) a benzyl ester at the carboxylate terminus, acting as an orthogonal protecting group that can be cleanly removed by catalytic hydrogenolysis (e.g., Pd/C, H₂) without disturbing acid-labile or base-labile functionality elsewhere in a molecule; and (3) a 3-(methylsulfonyl)phenyl side chain, which replaces the phenyl group of canonical phenylalanine with an electron-poor, strongly polar arene. The methylsulfonyl (–SO₂CH₃) moiety is a strong hydrogen-bond acceptor and electron-withdrawing group that significantly alters the electronic environment of the aromatic ring and augments aqueous solubility relative to unsubstituted phenylalanine. Together, these features make this compound a strategically differentiated amino acid building block for applications where introduction of a sulfonyl pharmacophore is desired.

Synthetic Applications and Role as a Building Block

The primary utility of this compound lies in its role as a protected, enantiopure amino acid monomer for use in solution-phase and solid-phase peptide synthesis (SPPS), as well as in the convergent assembly of peptidomimetics and small-molecule drug candidates.

Peptide coupling: With the amine presented as a hydrochloride salt and the carboxyl group masked as a benzyl ester, the free amine can be liberated by treatment with a mild base (e.g., N,N-diisopropylethylamine, DIPEA) and subsequently coupled to activated carboxylic acids using standard peptide coupling reagents such as HATU, HBTU, DIC/HOBt, or EDC. The benzyl ester is deprotected post-coupling by hydrogenolysis to unmask the carboxylic acid for further elongation or final deprotection.

Medicinal chemistry: The methylsulfonyl group is a well-established bioisostere and polar pharmacophore found in numerous approved drugs. Incorporation of this residue into peptide or peptidomimetic frameworks can modulate metabolic stability, binding affinity, and solubility. The compound therefore serves as an entry point for structure–activity relationship (SAR) studies targeting enzymes or receptors that accommodate arylsulfonyl motifs.

Asymmetric synthesis: As an enantiopure (S)-configured synthon, this compound can be used as a chiral template or resolved intermediate in total synthesis workflows where stereocontrol at the α-carbon is essential.

Handling, Storage, and Safety Considerations

As with most free amine hydrochloride salts and sulfonyl-containing organic compounds, standard good laboratory practice should be observed when handling this material.

• Personal protective equipment (PPE): Use appropriate gloves, safety glasses, and a laboratory coat. Handle in a well-ventilated area or fume hood to avoid inhalation of dust.
• Storage: Store the compound in a tightly sealed container, in a cool, dry location away from light and moisture. Refrigerated storage (2–8 °C) is typically recommended for long-term preservation of amino acid hydrochloride salts to prevent hydrolysis or racemization. Confirm specific storage conditions on the Certificate of Analysis (CoA) supplied with each lot.
• Stability: The hydrochloride salt form generally confers improved stability over the free base. The benzyl ester is susceptible to hydrolysis under strongly acidic or basic aqueous conditions and to hydrogenolysis; avoid prolonged exposure to such conditions unless intentional.
• Disposal: Dispose of waste in accordance with local institutional and regulatory requirements for organic chemical waste.

Note: A full Safety Data Sheet (SDS) should be consulted prior to use. Contact Aladdin Scientific for the SDS corresponding to SKU B770293.

Product Specifications and Ordering Information

(S)-Benzyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride is available from Aladdin Scientific under catalog number B770293. Researchers are encouraged to request the Certificate of Analysis (CoA) for each lot to verify purity (typically assessed by HPLC and/or NMR), optical rotation, and residual solvent content prior to use in critical synthetic steps.

When ordering, please specify the required quantity and confirm availability of current lot documentation. For bulk quantities, custom packaging, or additional technical support, contact the Aladdin Scientific sales team directly.