H-Asn-betaNA is an amino acid derivative in which asparagine (Asn) is conjugated to a beta-naphthylamide (betaNA) chromophore, forming an amide-linked reporter substrate rather than a free amino acid. The molecule contains an asparagine-derived amino functionality and a carboxamide side chain, while the overall structure presents an amide bond to the beta-naphthyl group and a free N-terminus indicated by the "H-" prefix. H-Asn-betaNA is used in biochemical and analytical workflows as a substrate for monitoring amino acid-related enzymatic activity or as a chromogenic/fluorogenic readout handle in assays that track cleavage or transformation of the beta-naphthylamide moiety.
CAT No: CP27008
CAS No:3313-39-1
Synonyms/Alias:L-Asparaginebeta-naphthylamide;3313-39-1;H-Asn-betaNA;AC1LELYH;L-asparagine-2-naphthylamide;L-Asparagine|A-naphthylamide;SCHEMBL9393008;CHEBI:90352;CTK8G0508;ZINC4899577;N(1)1-naphthalen-2-yl-L-aspartamide;FT-0634773;(2S)-2-amino-N-naphthalen-2-ylbutanediamide
H-Asn-betaNA is an N-terminally protected asparagine derivative in which the side chain is presented as an amide-containing Asn framework, enabling controlled peptide coupling while preserving the stereochemical integrity of the alpha-amino acid center. The "betaNA" motif indicates a beta-positioned functional handle that can participate in downstream derivatization or serve as a chemical reporter/recognition element depending on the conjugation chemistry used. The acetamide-type N-protection (H-Asn-betaNA) modulates amine reactivity during synthesis, supporting stepwise assembly of peptide sequences or the preparation of amino acid-based intermediates without uncontrolled side reactions. The combination of an amide side chain and a protected alpha-amino functionality yields a predictable reactivity profile for peptide bond formation and subsequent functional transformations typical of asparagine chemistry.
1. Peptide Synthesis
H-Asn-betaNA is used in peptide building and coupling workflows where the asparagine side-chain amide and the N-protected alpha-amino group enable reliable amide bond formation under standard peptide coupling conditions. The betaNA functional element can be retained through coupling steps to allow C-terminal or side-chain-directed modifications after sequence assembly. The protected amine reduces premature oligomerization and supports orthogonal deprotection strategies when constructing longer peptides or peptide fragments. Downstream, H-Asn-betaNA can be converted into defined Asn-containing peptide analogs suitable for structure-activity relationship studies and method development in peptide synthesis.
2. Chemical Biology Probes
H-Asn-betaNA is applicable to chemical biology research requiring amino acid-derived handles for tagging, affinity probes, or reporter conjugates. The asparagine amide provides a polar interaction motif that can influence solubility and recognition in biomolecular contexts, while the betaNA functionality can be exploited for selective attachment to biomolecule scaffolds. N-terminal protection helps maintain chemoselectivity during conjugation workflows, reducing background reactions from the free amine. Resulting conjugates and peptide-like constructs can serve as tools for mapping binding interfaces, monitoring biomolecular interactions, or generating molecular probes for biochemical assays.
3. Bioconjugation Chemistry
H-Asn-betaNA is suitable for bioconjugation strategies where controlled amino acid chemistry is needed to install a defined functional group onto proteins, peptides, or polymer backbones. The N-protected amino acid form supports stepwise functionalization, enabling the betaNA handle to be presented for coupling to electrophiles or activated partners while maintaining the integrity of the Asn side-chain amide. The presence of both a protected alpha-amine and an unmodified side-chain amide supports orthogonality between conjugation steps and later deprotection or activation steps. Bioconjugation products derived from H-Asn-betaNA can be used in biomolecule labeling, assay reagent preparation, and the generation of functional macromolecular materials.
4. Protected Amino Acid Intermediate
H-Asn-betaNA functions as a protected amino acid intermediate for synthesis planning in fine chemical and peptide-related manufacturing, where predictable reactivity and controlled chemoselectivity are required. The N-protected alpha-amino group supports storage and handling as a building block while the side-chain amide remains available for hydrogen-bonding interactions and for later transformations if conversion to activated derivatives is desired. The betaNA motif can act as a latent functional group that participates in downstream derivatization, enabling the preparation of specialized Asn-based intermediates for peptide analogs or functionalized scaffolds. The compound's structure aligns with industrial and research workflows that rely on protected amino acid derivatives for consistent batch-to-batch coupling performance.
5. SAR Peptidomimetics
H-Asn-betaNA is applicable to peptidomimetic and SAR-focused scaffold construction where Asn residues and side-chain amide chemistry are used to tune polarity, hydrogen-bonding networks, and conformational preferences. The N-protected amino acid format supports incorporation into peptide-like sequences, while the betaNA element can be leveraged to introduce a defined stereoelectronic or recognition feature into the analog. Chemoselective coupling enabled by the protected alpha-amino group supports systematic variation of neighboring residues and functional handles during analog generation. Peptidomimetics derived from H-Asn-betaNA can be used as defined chemical entities for SAR studies, molecular design campaigns, and comparative binding or stability evaluations in biochemical research settings.
6. Analytical Research Standards
H-Asn-betaNA can be employed in analytical research as a reference material or derivatization precursor for monitoring Asn-containing species and betaNA-bearing motifs in complex mixtures. The structured combination of an N-protected amino acid backbone and a functional beta handle supports reproducible mass spectrometric or chromatographic behavior after appropriate derivatization. The side-chain amide and controlled amine protection can reduce heterogeneity during sample preparation, supporting consistent detection of peptide fragments or conjugation products. Analytical standards or internal references generated from H-Asn-betaNA can support method validation, impurity profiling, and characterization of peptide synthesis intermediates and final products.
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