Bz-Ala-betaNA is a benzoyl-protected alanine derivative featuring an N-benzoyl (Bz) group on the amino terminus and a βNA (β-naphthylamine) functional handle on the side chain, classifying it as a modified amino acid substrate-like building block rather than a free amino acid. The molecule contains an alanine backbone with a carboxyl group and an anilide/amide-type linkage pattern arising from the benzoyl protection, and its βNA substituent provides an aromatic amine functionality that can participate in analytical detection or derivatization chemistry. In biochemical and peptide-chemistry workflows, Bz-Ala-betaNA is used as a structurally defined amino acid derivative for substrate analog studies and for preparing or evaluating more complex alanine-containing intermediates where a benzoyl-protected amino group and a βNA labeling handle are required.
CAT No: CP26738
CAS No:201988-47-8
Synonyms/Alias:BZ-ALA-BETANA;Benzoyl-L-alaninebeta-naphthylamide;201988-47-8;CTK8E6810;ZINC2560875;6479AH;AKOS025294848;RT-011446
Bz-Ala-betaNA is an N-benzyl oxycarbonyl (Bz) protected alanine derivative bearing a beta-naphthylamine (betaNA) functionality that introduces an aromatic, nucleophilic anilide-like motif alongside the chiral alanine stereocenter. The molecule combines a protected amino group with a carboxyl-bearing alanine framework, enabling controlled peptide coupling chemistry while maintaining the aromatic betaNA handle for subsequent derivatization or analytical readouts. The benzoyl-type N-protection strategy supports amide bond formation under peptide-synthesis conditions and can be removed or transformed to reveal reactive amine functionality for downstream assembly. The presence of the betaNA aromatic amine can participate in nucleophilic substitution, acylation, and conjugation reactions, making the compound suitable for building chiral amino acid intermediates and aromatic-tagged peptide analogs.
1. Peptide Synthesis
Bz-Ala-betaNA is used in peptide building block preparation where the Bz-protected alanine amino group supports stepwise peptide coupling without uncontrolled side reactions. The alanine backbone provides the stereodefined chiral center for constructing defined polypeptide sequences, while the carboxyl functionality can be converted into activated coupling partners compatible with standard amide bond formation. The betaNA aromatic amine can remain as a functional tag during assembly, enabling later modification after the peptide chain is established. The resulting peptide derivatives can serve as reference compounds for method development in peptide coupling chemistry and for generating aromatic-substituted analog libraries in synthetic organic chemistry.
2. Amino Acid Derivatization
Bz-Ala-betaNA is applied to amino acid derivatization workflows that require an orthogonally protected amine and a persistent aromatic nucleophile for selective functional group transformation. The N-protection pattern helps control chemoselectivity during acylation, esterification, or coupling steps that target the carboxyl or exposed nucleophiles at later stages. The betaNA moiety can undergo acylation or nucleophilic conjugation to install linkers, reporter groups, or additional side-chain functionality without disturbing the alanine stereochemistry. Downstream products include functionalized amino acid intermediates and aromatic-tagged derivatives suitable for fine chemical synthesis and structure-guided scaffold elaboration.
3. Chemical Biology Probes
Bz-Ala-betaNA is suitable for chemical biology research where aromatic amine-containing amino acid derivatives can function as recognition elements, labeling handles, or assay-compatible tags. The compound's protected alanine framework enables incorporation into peptide-like constructs that maintain defined stereochemistry for molecular recognition studies. The betaNA aromatic group can be leveraged for conjugation to probes, affinity reagents, or detection-compatible motifs, supporting downstream generation of labeled biomolecule analogs. The combination of a peptide-compatible backbone and an aromatic nucleophile supports the construction of probe candidates for biochemical investigation of binding motifs and interaction surfaces.
4. Analytical Research Standards
Bz-Ala-betaNA is used to prepare analytical standards and reference intermediates for monitoring amino acid derivatization, peptide coupling, and deprotection workflows. The presence of the betaNA aromatic functionality provides a chemically distinctive chromophore/amine handle that can facilitate detection by common analytical methods used in amino acid and peptide process development. The Bz-protected alanine segment contributes a well-defined protected-amino acid signature that can be tracked during synthetic sequence optimization. Reference derivatives generated from Bz-Ala-betaNA can support method validation for quantitation of protected intermediates and characterization of peptide-like products in research and industrial quality control contexts.
5. Pharmaceutical Intermediate Preparation
Bz-Ala-betaNA is applicable to pharmaceutical intermediate preparation where protected amino acid derivatives are required for controlled assembly of peptidomimetic or peptide-like structures. The Bz-protected alanine amino group supports chemoselective coupling steps, while the chiral center enables stereodefined synthesis of analogs used in medicinal chemistry programs. The betaNA aromatic amine can serve as a handle for further functionalization, enabling downstream formation of substituted aromatic motifs that are common in structure-activity relationship studies. The compound therefore functions as a chiral, protected amino acid-based intermediate that can be routed into larger synthetic sequences for fine chemical manufacturing and process chemistry development.
6. Peptidomimetics And SAR Studies
Bz-Ala-betaNA is employed in peptidomimetic construction and SAR studies requiring incorporation of stereodefined alanine units bearing an aromatic functional handle. The protected amino group and carboxyl-bearing backbone facilitate transformation into coupling-ready fragments that can be assembled into constrained or aromatic-substituted analogs. The betaNA moiety can be retained or modified to tune electronic and steric properties of the resulting scaffold, supporting systematic variation of molecular features during analog generation. The resulting peptidomimetic derivatives can be used as chemically defined candidates for structure-activity relationship investigations and for building fragment libraries in synthetic organic chemistry.
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