Boc,Bzl-L-Ala-OH is a protected L-alanine derivative in which the amino group is protected as a Boc (tert-butoxycarbonyl) carbamate and the carboxyl group is present as a benzyl (Bzl) ester, classifying it as a Boc-protected, O-benzyl-protected amino acid building block. The molecule contains the alanine backbone with a methyl side chain and retains the stereochemical designation "L" as indicated in the name, while the Boc and benzyl ester groups mask the amino and carboxyl functionalities to control chemoselectivity during stepwise assembly. It is used in peptide synthesis workflows as a protected amino acid intermediate, supporting sequential coupling by keeping the protected functional groups from participating in side reactions prior to deprotection at the appropriate stage.
CAT No: CP25415
CAS No:159999-80-1
Synonyms/Alias:159999-80-1;BOC,BZL-L-ALA-OH;AmbotzBAA1283;SCHEMBL4526992;CTK0B0042;MolPort-008-267-403;6228AH;ZINC12954760;A-8582;Na-(tert-Butyloxycarbonyl)-Na-benzyl-L-alanine;L-Alanine,N-[(1,1-dimethylethoxy)carbonyl]-N-(phenylmethyl)-
Chemical Name:N-(t-Butyloxycarbonyl)-N-benzyl-L-alanine
Boc,Bzl-L-Ala-OH is a protected L-alanine building block featuring a Boc (tert-butoxycarbonyl) group on the amino functionality and a benzyl (Bzl) ester protection on the carboxyl group. This doubly protected alanine derivative is designed for peptide chemistry workflows where controlled reactivity and compatibility with standard coupling conditions are required, making it a practical intermediate for assembling alanine-containing sequences and for preparing defined peptide segments.
1. Solid-Phase Peptide Segments
Boc,Bzl-L-Ala-OH is used by peptide synthesis groups to introduce an alanine residue in protected form during segment preparation and in workflows that rely on orthogonal handling of protecting groups. Its Boc-protected amino group supports controlled peptide bond formation after activation of the carboxyl functionality in downstream steps, while the benzyl ester protection helps maintain the residue's integrity during intermediate manipulations. Researchers commonly employ this type of protected alanine for constructing short peptide fragments, generating defined building blocks for custom peptide synthesis, and supporting reproducible assembly of alanine-rich motifs in structure-activity relationship studies.
2. Solution-Phase Coupling Intermediates
Boc,Bzl-L-Ala-OH serves as a practical intermediate for solution-phase peptide synthesis and medicinal chemistry research, where defined amino acid equivalents are required for consistent coupling performance and purification profiles. The dual protection pattern supports the preparation of alanine-containing intermediates that can be carried forward into subsequent coupling steps to build larger peptide or peptidomimetic scaffolds. Chemical development teams also use protected amino acid derivatives like this to streamline procurement of standardized building blocks for iterative library synthesis, where maintaining residue protection through multiple reaction and purification cycles is essential.
3. Pharmaceutical Peptide Building Blocks
Boc,Bzl-L-Ala-OH is frequently selected by teams developing peptide-based candidates and peptide-derived intermediates because it provides a stable, well-defined alanine unit for downstream assembly of drug discovery tool compounds and preclinical research materials. In these workflows, protected amino acid building blocks are used to ensure that the alanine residue participates in the intended coupling step without competing side reactions from free amino or carboxyl groups. The Boc/Bzl protection pattern supports controlled progression from residue-level synthesis toward fully protected peptide intermediates used for further functionalization and final deprotection strategies in custom manufacturing research.
4. Analytical Reference Material Preparation
Boc,Bzl-L-Ala-OH is also used in analytical chemistry and peptide method development contexts as a defined protected alanine standard for preparing calibration or reference materials tied to peptide synthesis intermediates. Laboratories working on LC-MS/MS method development, impurity profiling, or protecting-group stability studies often require structurally specific standards that reflect the protected residue form encountered during synthesis and purification. Using a defined Boc/Bzl alanine derivative helps ensure that reference signals correspond to the same protection state as the intermediates present in real peptide manufacturing workflows.
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