Boc,Bzl-D-Ala-OH is a protected derivative of the amino acid alanine in the D stereochemical configuration, featuring an N-terminal Boc (tert-butoxycarbonyl) carbamate and a side-chain-free methyl group typical of alanine. The molecule contains both a carboxylic acid functional group and a benzyl (Bzl) protected form consistent with a benzyl-protected carboxyl-related functionality, with the free amino functionality masked by the Boc group to control chemoselectivity during peptide assembly. In peptide chemistry, this protected amino acid derivative is used as a stepwise building block that supports selective coupling at the protected amine while the protecting groups help minimize undesired side reactions and facilitate preparation of alanine-containing peptide intermediates and analogues.
CAT No: CP25210
CAS No:120571-59-7
Synonyms/Alias:N-Boc-N-Bzl-D-alanine
Chemical Name:N-t-Butyloxycarbonyl-N-benzyl-D-alanine
Boc,Bzl-D-Ala-OH is a protected D-alanine building block bearing a Boc group on the amino terminus and a benzyl (Bzl) ester on the carboxyl side, providing orthogonal protection that is commonly leveraged in controlled peptide assembly workflows. The D-configuration at the alpha carbon makes it particularly useful for introducing stereochemical inversion into peptide sequences where resistance to proteolysis or altered conformational behavior is a design consideration. As a protected amino acid derivative, it is typically handled as a synthetic intermediate rather than a free amino acid reagent for direct biochemical supplementation.
1. Stereodefined Peptide Synthesis
Boc,Bzl-D-Ala-OH is used by peptide chemists to incorporate D-alanine residues into peptide chains with defined stereochemistry, supporting the preparation of stereochemically mixed or D-enriched peptide segments. Its Boc-protected amino functionality aligns with standard peptide coupling strategies for building protected peptide intermediates, while the benzyl ester carboxyl protection supports downstream transformations during segment condensation or stepwise assembly. Research groups focused on peptide structure-property relationships, including conformational studies and stereochemical control in synthetic peptides, commonly select this protected D-alanine derivative to ensure the D-configuration is retained through synthesis and purification.
2. Peptide Fragment Building Block
Boc,Bzl-D-Ala-OH is frequently employed to generate peptide fragments and protected intermediates used in solution-phase or custom peptide manufacturing workflows where discrete coupling units are prepared and later assembled into longer sequences. The dual protection pattern helps maintain functional-group compatibility during iterative synthesis, allowing chemists to manage reactivity across multiple residues while assembling D-Ala-containing motifs. This makes the reagent particularly relevant for constructing segments for library synthesis, where consistent stereochemistry at the D-alanine position and reliable handling of protected functionalities are essential for reproducible downstream coupling.
3. Pharmaceutical Intermediate Development
Boc,Bzl-D-Ala-OH is also used in medicinal chemistry and pharmaceutical intermediate development as a stereodefined amino acid unit for preparing D-alanine-containing intermediates en route to peptidomimetic scaffolds or peptide-based candidates. Process development teams and synthetic chemistry groups value protected amino acid derivatives for enabling controlled functional-group manipulation and sequencing of synthetic steps, especially when multiple reactive sites must be managed without premature deprotection. In this context, Boc,Bzl-D-Ala-OH serves as a practical, well-defined building block for constructing stereochemically specific intermediates that can be carried forward into subsequent coupling, deprotection, or derivatization steps.
4. Analytical Reference for D-Ala Motifs
Boc,Bzl-D-Ala-OH is used in analytical method development and characterization workflows where stereochemically defined protected D-alanine residues are required as reference materials for verifying peptide segment composition and protecting-group handling. Peptide characterization laboratories may employ this reagent to support method qualification for LC-based workflows, to generate known standards for fragment analysis, or to confirm retention of the D-configuration during synthetic sequence assembly. Because the compound is a defined, protected D-alanine derivative, it can be particularly useful when establishing analytical criteria for D-Ala-containing intermediates and for troubleshooting stereochemical integrity in multi-step peptide synthesis.
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