H-Pro-4MbetaNA · HCl

H-Pro-4MbetaNA · HCl is a protected amino acid derivative consisting of proline bearing a 4-methyl-β-naphthylamine (4MβNA) substituent on the side chain, supplied as its hydrochloride salt. The molecule contains a secondary amine within the proline ring and a carboxyl functional group that is present as the amino acid hydrochloride counterion, with the "H-Pro-" motif indicating an N-terminally unprotected proline framework while the 4MβNA-bearing side chain provides a bulky aromatic amine handle. As a salt-stabilized, structurally modified amino acid building block, it is used in peptide and peptidomimetic synthesis and in chemical biology workflows where an anilino/aryl-amine functional group is incorporated for labeling, conjugation, or structure-activity studies.

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

CAT No: CP26130

CAS No:100930-07-2

Synonyms/Alias:100930-07-2;H-PRO-4M-BETANAHCL;H-Pro-4MbetaNA.HCl;L-Proline4-methoxy-beta-naphthylamidehydrochloride;CTK8E8774;7227AH;RT-013536;K-0201;L-Proline4-methoxy-|A-naphthylamidehydrochloride

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M.F/Formula
C16H19ClN2O2
M.W/Mr.
306.79

H-Pro-4MbetaNA · HCl is a hydrochloride salt of an N-terminally protected proline derivative in which the proline nitrogen is acylated by a protecting group (H-Pro-), and the side-chain bears a 4MbetaNA substituent that introduces an additional functional handle for downstream derivatization. The presence of the HCl salt form indicates a protonatable basic site, which can influence solubility, coupling behavior, and compatibility with acid-sensitive steps during protected amino acid synthesis. The chiral proline scaffold provides stereochemical control for peptide bond formation and for conformational bias in peptidomimetic or constrained peptide analogs. The substituted side-chain functionality can participate in further amino acid modification, enabling construction of larger structures through selective functional group transformations while maintaining the protected backbone required for peptide chemistry.

1. Protected Amino Acid Synthesis

H-Pro-4MbetaNA · HCl is applied in protected amino acid synthesis workflows where a proline-based chiral intermediate must remain compatible with peptide coupling conditions. The combination of an N-protected proline framework with a side-chain functional substituent supports orthogonal protection strategies, allowing selective activation of the backbone while deferring derivatization of the 4MbetaNA-bearing functionality. The hydrochloride salt form can be used to manage handling and controlled solvation during intermediate preparation, which can be relevant for process chemistry intermediate staging. Downstream, the compound can serve as a building block for generating protected amino acid derivatives that feed directly into stepwise peptide assembly and iterative side-chain modification sequences.

2. Peptide Synthesis

H-Pro-4MbetaNA · HCl is suitable for peptide synthesis, particularly for constructing constrained sequences that incorporate proline stereochemistry to modulate backbone conformations. The N-protected proline motif enables controlled peptide bond formation at the amino acid backbone while the side-chain substituent provides a chemically addressable site for post-coupling functionalization. Salt formation with HCl can affect the deprotection and coupling window by influencing protonation states, which may be leveraged to coordinate protection-group removal and activation steps in a synthetic campaign. Resulting peptide products can be used as research-grade intermediates for SAR studies, peptidomimetic libraries, and conformationally biased peptide analogs where side-chain functionality is retained for later conjugation or analytical tagging.

3. Chemical Biology Conjugation

H-Pro-4MbetaNA · HCl can be used in chemical biology research where amino acid-derived conjugation handles are required for attaching probes to biomolecular scaffolds. The proline-based chiral center and the substituted 4MbetaNA side-chain functionality can support selective derivatization to generate conjugatable motifs while the protected backbone helps maintain structural integrity during multi-step labeling. The hydrochloride salt form can facilitate reproducible dissolution for conjugation reagent preparation and can be compatible with downstream neutralization and functional group activation strategies. Labeled peptide or peptide-like constructs derived from this intermediate can then be applied in biomolecule modification studies, molecular recognition assays, or mechanistic investigations that require stereodefined amino acid incorporation.

4. Peptidomimetics And SAR Studies

H-Pro-4MbetaNA · HCl serves as a chiral building block for peptidomimetic construction, where proline's conformational constraints and side-chain functionality are leveraged to tune molecular shape and interaction patterns. The protected amino acid structure supports sequential assembly of analogs that preserve stereochemistry at the proline center, enabling structure-activity relationship studies that correlate side-chain modifications with binding or recognition outcomes in vitro. The 4MbetaNA substituent can be retained as a functional group for further transformation into analog series, including modifications that alter polarity, sterics, or conjugation chemistry. Peptidomimetic scaffolds prepared from this intermediate can feed medicinal chemistry campaigns focused on fragment elaboration, molecular design exploration, and systematic SAR mapping.

5. Process Chemistry Intermediate

H-Pro-4MbetaNA · HCl is relevant to process chemistry intermediate preparation where isolable, chiral, protected amino acid derivatives are required for scalable manufacturing routes. The hydrochloride salt form provides a defined ionic state that can improve handling characteristics and can be incorporated into purification and material-transfer steps during industrial synthesis planning. The N-protected proline backbone supports predictable reactivity under peptide coupling regimes, while the side-chain functional group can be carried through as a controlled intermediate for later conversion to target derivatives. Downstream, this compound can be used to manufacture fine chemical intermediates for peptide building block supply, enabling consistent feedstock generation for peptide synthesis, peptidomimetic production, and specialty chemical production pipelines.

Size
250 mg;1 g;
InChI
1S/C16H18N2O2.ClH/c1-20-15-10-12(9-11-5-2-3-6-13(11)15)18-16(19)14-7-4-8-17-14;/h2-3,5-6,9-10,14,17H,4,7-8H2,1H3,(H,18,19);1H/t14-;/m0./s1
InChI Key
DKLGYZDYMFOBFD-UQKRIMTDSA-N
Canonical SMILES
COC1=CC(=CC2=CC=CC=C21)NC(=O)C3CCCN3.Cl

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