H-Dap-OH*HCl

H-Dap-OH*HCl is the hydrochloride salt of L-2,3-diaminopropanoic acid (DAP), presenting a chiral amino acid framework bearing two primary amino groups and a carboxylic acid functionality. The salt form protonates the amines, increasing water compatibility and enabling controlled reactivity during peptide coupling and derivatization. The presence of both α-amino and side-chain amino groups makes orthogonal protection strategies central to selective N-functionalization and to preventing undesired cross-linking. The amino acid hydrochloride also serves as a chiral, nitrogen-rich intermediate whose functional groups can be transformed into amide, urea, carbamate, or substituted amines for downstream synthetic and biochemical workflows.

1. Peptide Synthesis

H-Dap-OH*HCl is used in peptide building workflows where a diamino acid residue can be incorporated as a defined nitrogen-rich segment. The α-carboxylic acid and protonated amino groups support standard amino acid coupling logic after appropriate N-protection and salt management, enabling selective formation of peptide bonds at the intended nitrogen. Orthogonal protection of the side-chain amine allows controlled elongation of peptide chains while preserving the second amino group for later deprotonation, coupling, or post-assembly functionalization. The resulting protected DAP derivatives can be carried through iterative synthesis to generate peptide analogs and branching motifs that rely on side-chain nucleophilicity.

2. Amino Acid Modification

H-Dap-OH*HCl supports amino acid derivatization programs aimed at converting the diamino motif into targeted functional handles for further synthesis. The carboxylic acid can be activated for amide formation, while the two amino groups can be selectively masked as carbamates, Boc-type or Cbz-type protecting groups, or converted into urea and sulfonamide linkages depending on the desired reactivity profile. Salt-controlled protonation behavior helps manage chemoselectivity during sequential transformations, particularly when one amino group must remain available for conjugation or for constructing heteroatom-rich linkers. Downstream derivatives can function as intermediates for chiral amine libraries, cross-linker precursors, or nitrogen-functionalized scaffolds used in applied chemical synthesis.

3. Bioconjugation Chemistry

H-Dap-OH*HCl is applicable to bioconjugation and chemical biology workflows that require introduction of a stable, nucleophilic amino acid unit onto biomolecule surfaces. The diamino acid structure enables attachment strategies that rely on amine reactivity, including formation of amide or urea linkages after carboxyl activation or conversion to activated esters and coupling reagents. Side-chain amine availability supports conjugation to electrophilic tags, affinity handles, or polymer backbones, while orthogonal protection can preserve one amine for stepwise labeling. The hydrochloride salt form can facilitate handling in aqueous-compatible steps, supporting preparation of labeled peptides, reagent-grade linkers, and biomolecule-modification intermediates.

4. Process Chemistry Intermediate

H-Dap-OH*HCl is suitable for process chemistry intermediate preparation where a chiral, nitrogen-rich amino acid salt is needed as a feedstock for protected amino acid synthesis. The defined stereochemistry of the amino acid backbone and the predictable salt-state behavior assist route design for downstream N-protection, controlled deprotonation, and selective functional group transformations. The dual amino functionality enables manufacturing of a range of protected derivatives using systematic protection-group selection to minimize side reactions such as intramolecular cyclization or bis-functional coupling. The resulting intermediates can be used to produce peptide-grade building blocks, fine-chemical amine derivatives, and industrially relevant nitrogen-containing scaffolds for specialty chemical production.

5. Analytical Research Standards

H-Dap-OH*HCl can serve in analytical research as a reference material for method development involving amino acid quantification, derivatization chemistry, and chromatographic or spectrometric characterization. The hydrochloride salt form and the presence of two primary amino groups provide a consistent chemical signature for derivatization workflows that target amine functionality, including derivatization to improve detection in LC or GC methods. The carboxylic acid and diamino motif support calibration strategies for assessing recovery, stability, and conversion completeness during protected amino acid processing. Downstream use extends to verifying identity and stereochemical integrity of DAP-containing intermediates and to supporting quality control of peptide synthesis inputs and amino acid derivative batches.

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