H-beta-Ala(SO3H)-OH

H-beta-Ala(SO3H)-OH is a β-alanine derivative bearing a sulfonic acid substituent on the β-position, yielding a strongly polar, anionic side chain that remains solvated across a wide pH range. The molecule contains the amino acid backbone with a free carboxylic acid and a β-amino group, enabling direct participation in peptide coupling chemistry and subsequent functional group transformations. The sulfonic acid group provides a persistent negative charge, supports salt formation, and can influence solubility, ion pairing, and chromatographic behavior in analytical workflows. As a chiral or non-chiral amino acid intermediate depending on the stereochemical context of the β-substitution, H-beta-Ala(SO3H)-OH can be used as a chemically defined building block for introducing sulfonate functionality into peptides, peptidomimetics, and highly polar biomolecular constructs.

1. Peptide Synthesis

H-beta-Ala(SO3H)-OH is applied in peptide synthesis where the amino acid backbone supports standard amide bond formation after appropriate amino and carboxyl activation. The sulfonic acid side chain can be protected or used in situ depending on coupling conditions, since its strong acidity may affect coupling reagent compatibility and solubility during peptide assembly. Incorporation of the β-sulfonate-bearing residue enables construction of peptide segments that mimic acidic, highly hydrated motifs and can be used to tune charge density and electrostatic interactions. Downstream, the resulting sulfonated peptides serve as research-grade materials for studying sequence-dependent binding, solubility control, and post-synthetic ion-exchange behavior typical of sulfonate-rich biomolecules.

2. Amino Acid Derivatization

H-beta-Ala(SO3H)-OH serves as a direct substrate for amino acid derivatization strategies that target the sulfonate and carboxyl functionalities without losing the β-alanine scaffold. The free carboxylic acid enables formation of activated esters or amide derivatives for producing labeled or immobilized analogs, while the sulfonic acid can be exploited for salt formation, ion-pairing studies, and controlled hydrophilicity. Protecting-group strategies may include temporary masking of the amino or carboxyl group to improve chemoselectivity during multi-step functionalization, followed by deprotection to restore a charged sulfonate handle. The resulting derivatives can function as biochemical research intermediates, ion-exchange probes, or functional building blocks for generating sulfonated libraries used in synthetic organic chemistry and materials-oriented screening.

3. Chemical Biology Probes

H-beta-Ala(SO3H)-OH is suitable for chemical biology probe development where a stable sulfonate group is used to modulate membrane interactions, protein surface recognition, and aqueous solubility. The β-amino acid framework supports conjugation to biomolecular targets through peptide-like linkers, while the sulfonic acid provides a persistent anionic moiety that can reduce nonspecific hydrophobic interactions. Selective protection of the amino and carboxyl groups can enable stepwise coupling to labels, affinity handles, or immobilization matrices while retaining the sulfonate charge for consistent binding behavior. Generated sulfonate-bearing conjugates can be used in assays that evaluate electrostatic contributions to molecular recognition, including structure-activity relationship studies for charged ligand series and mapping of interaction hotspots on proteins or nucleic-acid-associated complexes.

4. Analytical Standards

H-beta-Ala(SO3H)-OH functions as an analytical reference material and method development intermediate for quantifying sulfonated amino acid motifs and monitoring derivatization workflows. The combination of a carboxylic acid and a sulfonic acid produces characteristic ionization patterns that can be leveraged for LC-MS or ion chromatography method tuning, including predictable retention and detector response for strongly acidic analytes. Chemically defined handling of the β-alanine backbone also supports reproducible preparation of calibration mixtures and internal standards for studies involving sulfonate-containing peptides or polymer fragments. Downstream use includes preparing labeled or derivative forms that improve assay specificity when tracking sulfonate incorporation during peptide construction, polymer modification, or process monitoring.

5. Process Chemistry Intermediate

H-beta-Ala(SO3H)-OH is relevant to process chemistry and specialty chemical production as a charged amino acid intermediate for manufacturing sulfonated building blocks. The sulfonic acid group enables downstream conversion into salts, ion-exchange precursors, or sulfonate-functional intermediates used in fine chemical synthesis, while the amino acid backbone supports conversion into protected derivatives for controlled coupling steps. Protection and deprotection strategies can be designed to manage chemoselectivity between the sulfonate, amino, and carboxyl groups during scale-up, including routes that minimize side reactions caused by strong acidity. The resulting downstream intermediates can be employed to produce sulfonate-rich peptide analogs, highly polar conjugates, or functional materials precursors where consistent ionic character is required for reproducible manufacturing and downstream formulation behavior.

1. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes

2. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

3. An Open-label, Single-center, Safety and Efficacy Study of Eyelash Polygrowth Factor Serum

4. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

5. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients