H-Thr-betaNA contains a threonine-derived amino acid framework linked to a β-naphthylamide (βNA) reporter, classifying it as an amino acid amide derivative rather than a free amino acid. The molecule bears a terminal N-α amino group (as indicated by the H- prefix) and a carboxamide functionality at the side-chain reporter position, with threonine's β-hydroxyl side chain providing an additional hydrogen-bonding handle for analytical and enzymatic substrate recognition studies. H-Thr-betaNA is used as a chromogenic or fluorogenic-style substrate analog in biochemical assay development where the β-naphthylamide moiety enables monitoring of amino acid-related transformations or cleavage events under controlled in vitro conditions.
CAT No: CP27403
CAS No:729-25-9
Synonyms/Alias:L-Threoninebeta-naphthylamide;729-25-9;H-Thr-betaNA;AC1ODVCG;N-threonyl-2-aminonaphthalene;SCHEMBL12538852;CHEBI:90604;N-(2-naphthyl)-L-threoninamide;N-(beta-naphthyl)-L-threoninamide;N-naphthalen-2-yl-L-threoninamide;ZINC2572095;7347AH;(2S,3R)-2-amino-3-hydroxy-N-naphthalen-2-ylbutanamide;(2S,3R)-2-amino-3-hydroxy-N-(naphthalen-2-yl)butanamide
H-Thr-betaNA is a protected threonine-derived amino acid derivative in which the threonine backbone is coupled to a beta-naphthylamide (betaNA) motif, providing a chiral, amide-bearing building block with a defined stereocenter at the threonine alpha-carbon. The structure contains the threonine side-chain hydroxyl functionality, which can participate in selective protection/deprotection logic and can be used as a handle for further derivatization while maintaining orthogonality to the amide linkage. The N-terminal amino group is presented as an N-acylated or N-protected form consistent with peptide-coupling compatibility, enabling controlled transformations without premature oligomerization. The aromatic beta-naphthylamide portion increases hydrophobic character and can serve as a spectroscopically or chromatographically detectable tag, while the overall functional-group pattern supports downstream conversion into peptide analogs and synthetic intermediates for amino acid chemistry workflows.
1. Peptide Synthesis
H-Thr-betaNA is suitable for peptide building block preparation where threonine's alpha-amino and side-chain hydroxyl features are leveraged under peptide coupling conditions. The betaNA amide and the N-protected amino functionality enable controlled N-to-C coupling strategies while preserving the stereochemical integrity of the threonine residue. The side-chain hydroxyl can be managed through protecting-group selection to support selective deprotection and subsequent functionalization during chain elongation. Incorporation of this threonine derivative into short peptide fragments or peptide-like constructs supports fragment assembly, library synthesis, and systematic evaluation of threonine-containing sequences in peptide science and peptidomimetic construction.
2. Chemical Biology Probes
H-Thr-betaNA can function as a chemical biology substrate or probe precursor because the beta-naphthylamide motif provides an aromatic reporter region that can be used to monitor chemical transformations or binding-associated changes. The threonine-derived stereocenter and the side-chain hydroxyl enable chemically defined recognition patterns that can be carried through derivatization steps to generate substrate analogs for enzyme studies. The amide linkage and protected amino functionality support stable conjugate formation while allowing downstream modification of the side-chain hydroxyl to tune polarity and interaction profiles. Use of H-Thr-betaNA in biochemical research intermediate preparation can support reagent generation for mechanistic studies, structure-function investigations, and analytical readouts tied to amino acid derivative transformations.
3. Enzyme Substrate Analogues
H-Thr-betaNA is applicable to enzyme substrate or inhibitor design workflows where threonine's side-chain hydroxyl and the defined alpha stereochemistry are used to mimic key recognition elements. The betaNA amide portion can serve as a chromophoric or fluorogenic group in analytical assays, enabling monitoring of enzymatic processing of amino acid-derived motifs. The N-protected amino/amide framework supports incorporation into larger synthetic constructs that retain the stereochemical and functional-group context required for enzyme compatibility. Downstream, H-Thr-betaNA can be converted into a series of substrate analogs or peptidomimetic fragments for comparative studies of enzyme tolerance to side-chain modifications and backbone stereochemistry.
4. Amino Acid Derivatization
H-Thr-betaNA supports amino acid derivatization strategies that exploit the threonine side-chain hydroxyl for selective functional-group transformation while the betaNA amide provides a stable anchoring group. The presence of a defined chiral center and an amide-bearing N-terminus enables systematic exploration of stereochemical effects on downstream reactivity and molecular recognition. Protection and deprotection planning can be applied to the side-chain hydroxyl to generate O-alkyl, O-acyl, or O-linked substituents without disrupting the amide linkage that governs overall stability. The resulting derivatives can be used as intermediates for protected amino acid synthesis, fine chemical synthesis, and the construction of functionalized amino acid analogs for peptide science and chemical manufacturing routes.
5. Analytical Research Standards
H-Thr-betaNA is well-suited for analytical research and method development where the beta-naphthylamide aromatic region can improve detectability in chromatographic and spectroscopic workflows. The threonine-derived stereochemical definition helps ensure that analytical standards correspond to specific stereoisomeric identity, which is critical when evaluating amino acid derivative formation, coupling outcomes, or impurity profiles. The amide and hydroxyl functional groups enable consistent chemical behavior during sample preparation steps, supporting reproducible derivatization or detection schemes. Use of H-Thr-betaNA as an analytical standard or reference intermediate can support quality control of protected amino acid synthesis, peptide building block preparation, and downstream characterization of amino acid-derived products in research-grade supply chains.
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