Bzl,Me-L-Ala-OMe*HCl is a protected amino acid derivative based on L-alanine in which the amino group is benzylated (Bzl) and the carboxyl group is converted to a methyl ester (OMe), with the overall compound present as a hydrochloride salt. The molecule contains a benzyl-protected nitrogen and an esterified carboxyl functionality, and the salt form indicates protonation of the amino-derived basic site while retaining the stereochemical designation "L" at the alanine center. It is used as a stepwise building block in peptide and peptide-analog synthesis where chemoselective deprotection and subsequent coupling can be performed to assemble more complex amino acid and peptide derivatives, and the salt/ester format supports handling and controlled reactivity during synthetic sequences.
CAT No: CP25475
CAS No:175853-53-9
Chemical Name:N-Benzyl-N-methyl-L-alanine methyl ester hydrochloride
Bzl,Me-L-Ala-OMe*HCl is an L-alanine derivative presented as a hydrochloride salt, incorporating a benzyl (Bzl) N-protecting group and a methyl ester (OMe) at the carboxyl terminus. The molecule retains the stereogenic center of L-alanine, providing a defined chiral amino acid ester suitable for stereocontrolled peptide coupling and downstream transformations. The N-benzyl protection modulates amine reactivity during acylation steps, while the ester functionality enables selective hydrolysis or transesterification to access carboxylic acid or alternative activated forms. Salt formation improves handling of the amino ester in synthetic workflows and supports reproducible coupling chemistry typical of protected amino acid intermediates.
1. Peptide Synthesis
Bzl,Me-L-Ala-OMe*HCl serves as a chiral peptide building block precursor in solid-phase or solution-phase peptide synthesis where N-protection and C-terminal ester masking are required. The benzyl-protected amino group participates in standard peptide coupling after appropriate activation of the carboxyl function, while the methyl ester can be converted to a carboxylate or acid equivalent for amide bond formation strategies. The L-configuration at the alpha carbon supports stereochemical fidelity during chain elongation, and the hydrochloride form can be leveraged to manage amine protonation state during protection/deprotection and coupling sequences. Downstream, the benzyl group and ester group can be removed or transformed to generate defined peptide fragments and intermediates for longer peptide assembly.
2. Protected Amino Acid Chemistry
Bzl,Me-L-Ala-OMe*HCl functions as a protected amino acid intermediate for derivatization workflows that require orthogonal reactivity between the N-terminus and the C-terminus. The N-benzyl (Bzl) group suppresses undesired side reactions of the amino functionality, enabling selective manipulation of the ester moiety through hydrolysis to the corresponding acid or conversion to activated derivatives for further coupling. The methyl ester provides a handle for controlled downstream transformations such as transesterification or preparation of carboxyl-activated intermediates used in peptide bond construction. The salt form supports practical handling in fine chemical synthesis and enables reproducible conversion routes from protected amino acid ester to peptide-ready carboxylic acid equivalents.
3. Chiral Synthesis Intermediate
Bzl,Me-L-Ala-OMe*HCl is suitable for chiral building block development where maintaining L-stereochemistry is essential for stereocontrolled synthesis of amino acid derivatives and chiral auxiliaries. The defined stereocenter and protected amine/ester pattern allow the compound to be used as a starting point for stereospecific transformations that preserve configuration, including functional group interconversions at the carboxyl terminus and controlled deprotection of the N-protecting group. The benzyl protection can be removed under hydrogenolysis-compatible conditions in synthetic sequences, enabling access to amino acid forms used for subsequent derivatization. Downstream, the compound can be employed to generate enantiopure alanine-containing fragments for stereodefined peptide analogs, chiral reference materials, and process chemistry intermediate preparation.
4. Analytical Research Standards
Bzl,Me-L-Ala-OMe*HCl can be applied in analytical research as a chemically defined amino acid ester standard or reference material for method development involving protected amino acids and peptide coupling intermediates. The combination of benzyl N-protection, methyl ester functionality, and hydrochloride salt form provides characteristic chromatographic and spectroscopic signatures that can support identification and quantification of alanine-derived intermediates in complex reaction mixtures. The stereochemical integrity of the L-form can be relevant for enantiomeric or stereochemical verification workflows when comparing protected amino acid derivatives. Downstream, the compound's defined structure supports stability studies, impurity profiling, and analytical calibration in research-grade peptide chemistry and amino acid derivatization monitoring.
5. Pharmaceutical Intermediate Preparation
Bzl,Me-L-Ala-OMe*HCl is relevant to pharmaceutical intermediate preparation where alanine-based fragments are used in the synthesis of peptide-like building blocks and peptidomimetic scaffolds. The protected amino ester format supports controlled assembly of amide linkages while limiting side reactions during multistep synthesis, and the benzyl N-protection can be managed to align with orthogonal deprotection strategies in longer sequences. The methyl ester can be converted to carboxylic acid or activated forms to enable coupling to diverse electrophiles, supporting manufacturing route design for defined intermediates. Downstream, the compound can serve as a reproducible chiral starting material for generating alanine-containing intermediates used in specialty chemical production and fine chemical synthesis workflows that require stereodefined composition.
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