H-Pro-betaNA · HCl

H-Pro-betaNA · HCl is a protected amino acid derivative consisting of L-proline (H-Pro) bearing a beta-naphthylamide (betaNA) functionality and present as a hydrochloride salt, placing it within the proline-derived amino acid building-block class. The molecule contains an amide-linked betaNA substituent alongside the proline backbone nitrogen and a carboxyl group that is associated with chloride as the counterion, and the "H-" designation indicates an N-terminal amino functionality rather than a peptide-level N-protecting group. As a salt-form amino acid derivative, it is commonly used in peptide chemistry and substrate/labeling workflows where a proline-containing scaffold with a chromophoric or amide-bearing handle supports synthesis of more complex amino acid and peptide intermediates or analytical method development.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27616

CAS No:97216-16-5

Synonyms/Alias:L-Prolinebeta-naphthylamidehydrochloride;97216-16-5;L-Proline-2-naphthylamidehydrochloride;ST50320096;16037-15-3;C15H16N2O.HCl;P1380_SIGMA;CTK8G0654;MolPort-003-939-165;7340AH;AKOS024307515;L-Proline2-naphthylamidehydrochloride;DB-057667;FT-0642341;L-PROLINEBETA-NAPHTHYLAMIDEHYDROCHLORIDE;P-7500;((2S)pyrrolidin-2-yl)-N-(2-naphthyl)carboxamide,chloride;(2S)-N-(naphthalen-2-yl)pyrrolidine-2-carboxamidehydrochloride;2-Pyrrolidinecarboxamide,N-2-naphthalenyl-,hydrochloride(1:1)

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M.F/Formula
C15H17ClN2O
M.W/Mr.
276.77

H-Pro-betaNA · HCl is a hydrochloride salt of an L-proline-derived amino acid derivative in which the proline nitrogen is acylated or otherwise functionalized to present a protected, handleable amide-bearing scaffold, while the β-amino acid motif is associated with a β-nitrogen/amide/reactive side-chain functionality suitable for further derivatization. The presence of the HCl salt form establishes a protonated amine environment that can improve handling and reproducibility in peptide-related coupling workflows, while the stereochemically defined proline ring constrains conformational preferences relevant to peptide backbone organization. The carbonyl-containing functional groups participate in standard peptide coupling and acyl transfer chemistry, and the β-functional moiety can be carried through protection/deprotection sequences to access downstream amino acid building blocks or specialized peptidomimetic fragments. As a chiral, salt-stabilized intermediate, H-Pro-betaNA · HCl can serve as a practical precursor for amino acid derivatization, peptide construction, and synthetic methodology development where controlled incorporation of a proline-based β-amino unit is required.

1. Peptide Synthesis

H-Pro-betaNA · HCl is used in peptide synthesis workflows where proline-derived stereochemistry and amide-forming functionality support incorporation of a β-amino acid segment into growing peptide chains. The salt form and carbonyl-containing groups enable compatibility with common peptide coupling strategies, while the constrained proline ring can influence local backbone geometry and turn propensity in peptide analogs. The β-amino functionality can be protected or activated as needed to manage chemoselectivity during sequential N- and C-terminal modifications. Downstream, the resulting peptide building block intermediates can be applied to generate proline-containing peptides and peptide fragments for biochemical research and structure-guided scaffold development.

2. Chemical Biology Probes

H-Pro-betaNA · HCl is suitable for chemical biology applications that require incorporation of a defined chiral amino acid derivative into labeling handles or recognition elements. The β-amino/amide functionality can be transformed into electrophilic or conjugatable derivatives, enabling attachment to biomolecular targets such as peptides, proteins, or affinity ligands through controlled functional-group interconversions. The proline-based framework contributes conformational bias that can improve the fidelity of molecular recognition in probe design and can be carried through to maintain stereochemical integrity. The compound can therefore function as a chiral intermediate for generating biomolecule-modifying reagents and peptidic probes used in mechanistic studies.

3. Peptidomimetics And SAR

H-Pro-betaNA · HCl supports peptidomimetic construction for structure-activity relationship studies where proline stereochemistry and β-amino substitution patterns are used to tune binding conformations. The presence of amide-forming groups and a defined chiral center enables systematic derivatization at the β-position, supporting analog libraries that vary side-chain electronics, hydrogen-bonding capacity, and steric profile. Protection-group strategies can be applied to differentiate N-functionalization from β-functional modification, allowing selective functional group installation for SAR mapping. The resulting peptidomimetic fragments can be advanced as modular components in medicinal chemistry programs focused on conformationally constrained amino acid analogs.

4. Protected Amino Acid Chemistry

H-Pro-betaNA · HCl is applied as a chiral amino acid intermediate in protected amino acid synthesis, where salt formation and functional-group patterning facilitate controlled downstream transformations. The proline-derived ring and carbonyl functionality allow the compound to be carried through N-protection, side-chain protection, and selective deprotection sequences to access defined coupling-ready forms. The β-amino/amide motif can be selectively converted into activated derivatives or orthogonally protected intermediates, supporting chemoselective peptide coupling and fragment assembly. Downstream utility includes preparation of standardized amino acid building blocks, process-compatible intermediates, and stereochemically consistent inputs for fine chemical synthesis.

5. Pharmaceutical Intermediate Preparation

H-Pro-betaNA · HCl is relevant to pharmaceutical intermediate preparation where chiral, proline-based β-amino units are incorporated into synthetic routes for peptide-like or peptidomimetic candidates. The hydrochloride salt form can improve handling of the amine functionality during multi-step synthesis, while the carbonyl-bearing scaffold supports conversion into coupling reagents and downstream acylated intermediates. Functional-group compatibility with sequential protection/deprotection and activation steps makes the compound suitable for manufacturing-oriented planning of stereochemically defined intermediates. The resulting derivatives can serve as upstream building blocks for API-related syntheses and for the preparation of analytical standards used during process development and method validation.

Size
1 g;5 g;
InChI
1S/C15H16N2O.ClH/c18-15(14-6-3-9-16-14)17-13-8-7-11-4-1-2-5-12(11)10-13;/h1-2,4-5,7-8,10,14,16H,3,6,9H2,(H,17,18);1H/t14-;/m0./s1
InChI Key
UKXYCTFKKXKIPY-UQKRIMTDSA-N
Canonical SMILES
C1CC(NC1)C(=O)NC2=CC3=CC=CC=C3C=C2.Cl

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