D-Alanine-1-naphthylester hydrochloride is a D-configured alanine derivative in which the carboxyl group is esterified with 1-naphthol, forming an aryl ester while retaining the amino acid backbone and the methyl side chain characteristic of alanine. The molecule contains a free primary amino functionality associated with a hydrochloride counterion and an ester linkage to the naphthyl moiety, providing a hydrophobic aromatic handle alongside the amino acid-derived functional groups. This compound is used in peptide chemistry and analytical method development as a protected/derivatized alanine building block and as an aryl-ester substrate or labeling intermediate where the naphthyl group enables chromatographic detection or spectroscopic readouts.
CAT No: CP00132
D-Alanine-1-naphthylester hydrochloride is a chiral D-alanine derivative in ester form, where the carboxyl group is converted to a 1-naphthyl ester and the amino functionality is present as a hydrochloride salt. The molecule therefore combines a stereogenic α-carbon from the D-alanine backbone with an anilide-free, aromatic ester linkage that can participate in acyl transfer chemistry under suitable conditions. The naphthyl ester introduces a hydrophobic, π-rich aromatic handle that can be used for spectroscopic tracking, chromatographic behavior tuning, and downstream conversion to other carboxyl-derived derivatives after controlled ester cleavage. The hydrochloride counterion improves handling of the amino group and supports reproducible coupling and derivatization workflows in peptide-adjacent and analytical synthetic chemistry.
1. Peptide Coupling Chemistry
D-Alanine-1-naphthylester hydrochloride is applied in peptide coupling chemistry as a chiral D-alanine-based acyl precursor where the amino group is present in a salt form and the carboxyl functionality is masked as a naphthyl ester. The ester linkage can be transformed into an activated carboxyl equivalent or can be used to generate D-alanine-containing intermediates compatible with standard peptide coupling strategies. The D-configuration at the α-carbon supports stereochemically defined incorporation of D-alanine motifs into dipeptides, oligopeptides, and peptide fragments used for method development. The aromatic naphthyl group can also aid in monitoring reaction progress and purity by UV-active detection, linking protected amino acid synthesis logic to peptide building block preparation.
2. Chiral Amino Acid Derivatization
D-Alanine-1-naphthylester hydrochloride supports chiral amino acid derivatization workflows where the D-alanine stereocenter and the naphthyl ester provide a robust platform for stereochemical studies and derivative library generation. The naphthyl ester serves as a stable, hydrophobic tag that can modulate solubility and chromatographic retention, enabling separation of stereoisomeric amino acid derivatives in analytical or process scouting contexts. Salt formation with hydrochloride can facilitate reproducible handling during conversion to other functional forms, such as carboxylate equivalents or amino-protecting group strategies for subsequent synthetic steps. Downstream use includes preparation of stereochemically defined D-alanine derivatives for structure-activity relationship studies and for building chiral reference materials used in synthetic organic chemistry.
3. Analytical Standards And Labeling
D-Alanine-1-naphthylester hydrochloride is suitable for analytical research and method development where the 1-naphthyl chromophore provides strong UV absorbance and helps track amino acid ester species in complex mixtures. The ester form can be employed to generate labeled or derivatized analytes that reflect amino acid backbone integrity while introducing an aromatic reporter group for HPLC/UPLC quantification and fraction monitoring. The D-alanine stereochemical identity enables stereospecific analytical comparisons, including monitoring stereochemical outcomes in amino acid transformations and peptide-adjacent syntheses. The hydrochloride salt form can support consistent sample preparation, making the compound applicable to analytical standard development and to verification of derivatization or cleavage steps in amino acid chemistry.
4. Fine Chemical Intermediate Synthesis
D-Alanine-1-naphthylester hydrochloride functions as a chiral amino acid-based intermediate for fine chemical synthesis where the esterified carboxyl group and the D-stereocenter enable controlled downstream conversion into carboxylic acid derivatives. The naphthyl ester can be selectively cleaved or converted to other acyl-bearing functionalities, supporting the construction of D-alanine derivatives that feed into broader synthetic sequences for peptide analogs and chiral building blocks. The aromatic ester linkage can also be leveraged to tune reactivity and selectivity during intermediate preparation, since ester hydrolysis and acyl transfer chemistry can be engineered to match process constraints. Industrially relevant use cases include preparation of stereodefined intermediates for specialty chemical production and for manufacturing routes that require D-amino acid incorporation with traceable aromatic tagging.
5. Peptidomimetics for SAR Studies
D-Alanine-1-naphthylester hydrochloride can be employed in peptidomimetic construction for structure-activity relationship studies where D-alanine incorporation is used to probe conformational effects and protease resistance in peptide-like scaffolds. The compound's chiral D-alanine backbone provides a stereochemically defined residue, while the naphthyl ester can serve as a handle for generating acyl derivatives that are compatible with stepwise assembly of peptide analogs. The ability to convert the ester functionality into other carboxyl-derived forms supports iterative scaffold diversification, including synthesis of D-alanine-containing fragments used in SAR workflows. Aromatic tagging further supports analytical characterization of intermediate and final peptidomimetic products, linking chiral amino acid chemistry to downstream molecular design efforts.
1. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
4. Peptides as Active Ingredients: A Challenge for Cosmeceutical Industry
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