Boc-alpha-Et-D-Ala-OH is a protected amino acid derivative that contains a Boc (tert-butoxycarbonyl) carbamate protecting group on the amino functionality and an ethyl-substituted side chain consistent with an alanine analogue, with the D stereochemical configuration indicated by the product name. The molecule bears both a free carboxylic acid group and the Boc-protected amino group, while the side-chain features an ethyl substituent that alters steric and hydrophobic character relative to unmodified alanine. In peptide and amino-acid derivative synthesis, it functions as a stepwise building block in which the Boc protection helps control chemoselectivity during coupling and supports preparation of peptides or peptide-like structures incorporating the D-ethyl-alanine motif.
CAT No: CP25385
CAS No:151171-11-8
Synonyms/Alias:(S)-2-((tert-Butoxycarbonyl)amino)-2-methylbutanoicacid;151171-11-8;(S)-2-(tert-butoxycarbonylamino)-2-methylbutanoicacid;Boc-L-isovaline;SCHEMBL1979479;MolPort-008-155-791;SHZXLTCEPXVCSV-JTQLQIEISA-N;ZINC34623327;AKOS024465011;AK163818;(S)-2-Methyl-2-(tert-butoxycarbonylamino)butyricacid
Chemical Name:(S)-2-(t-Butyloxycarbonylamino)-2-methylbutanoic acid
Boc-alpha-Et-D-Ala-OH is a Boc-protected D-alanine derivative bearing an ethyl-substituted alpha side chain, providing a stereochemically defined, non-proteinogenic amino acid building block for peptide and peptidomimetic synthesis. The N-terminal Boc protection supports controlled incorporation during protected amino acid assembly workflows, while the D-configuration and modified alpha substitution enable structure-property studies where stereochemistry and steric/electronic effects are intentionally varied. This reagent is commonly used by medicinal chemistry and peptide chemistry teams preparing non-natural peptide analogs and pharmaceutical intermediates that require precise stereochemical control.
1. Peptidomimetic Building Blocks
Boc-alpha-Et-D-Ala-OH is used as a non-natural amino acid building block in peptidomimetic and modified peptide synthesis, where researchers aim to tune backbone geometry and local steric environment relative to standard alanine. Medicinal chemistry groups and custom peptide synthesis providers incorporate this D-configured, Boc-protected unit into peptide analogs to probe structure-activity relationships and to generate analog series for downstream biological evaluation workflows. The Boc protection supports standard protected-amino-acid handling during peptide assembly, while the alpha-ethyl substitution provides an additional handle for modulating conformational preferences and physicochemical properties of the resulting peptide scaffold.
2. Solid-Phase Peptide Synthesis Inputs
Boc-alpha-Et-D-Ala-OH is frequently selected as a protected amino acid input for solid-phase peptide synthesis campaigns that require incorporation of a stereochemically defined, non-proteinogenic residue. Peptide synthesis teams use this type of Boc-protected building block when preparing short-to-medium peptide segments and when constructing modified backbones for SAR studies, chemical biology probes, or reference standards used in analytical method development. The D-configuration and alpha-ethyl substitution help ensure that the installed residue remains distinct from proteinogenic alanine, supporting reproducible synthesis of analogs where stereochemistry and backbone substitution pattern are key variables.
3. Pharmaceutical Intermediate Development
Boc-alpha-Et-D-Ala-OH is also used in pharmaceutical intermediate development as a controlled stereochemical building block for assembling non-natural peptide fragments and advanced intermediates. Process and development chemists rely on such protected amino acid derivatives to generate well-defined coupling-ready segments that can be carried forward into larger synthetic sequences, including the preparation of peptide-based drug candidates and related research materials. The combination of Boc protection and defined D-stereochemistry supports downstream synthetic consistency, which is particularly valuable when producing analog libraries or when scaling the preparation of specific modified-residue intermediates for subsequent purification and characterization steps.
4. Analytical Reference Standards
Boc-alpha-Et-D-Ala-OH is used to prepare defined peptide standards and intermediate references for analytical workflows that require non-natural residue specificity. Analytical chemistry laboratories and method development teams incorporate this building block into model peptides or calibration constructs to validate LC-MS/MS workflows, confirm identity of modified peptide fragments, and support characterization of synthetic batches containing D-configured, alpha-substituted alanine analogs. Because the residue is non-proteinogenic and stereochemically defined, it helps distinguish target-containing materials from proteinogenic background components during method qualification and routine analytical verification.
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