3-Carboxypropanesulfonamide

3‑Carboxypropanesulfonamide (3‑CPS) is a small, zwitterionic sulfonamide whose structure contains a carboxylic acid at one terminus and a sulfonamide group at the opposite end of a three‑carbon propyl spacer. The compound is water‑soluble, chemically stable under neutral to mildly basic conditions, and exhibits a moderate antimicrobial profile against Gram‑positive bacteria and certain fungal strains. In the laboratory it is commonly employed as a synthetic building block for the preparation of more complex sulfonamide derivatives, as a model compound for physicochemical studies of sulfonamides, and as a reagent in organic synthesis. Its modest size and polarity make it an attractive scaffold for probing protein‑ligand interactions in drug‑design campaigns, particularly for enzymes that accommodate small anionic ligands.

Appearance

• White to off‑white crystalline powder

• Slightly hygroscopic; forms a clear solution in water

Source

• Commercially available from specialty chemical suppliers (e.g., Sigma‑Aldrich, TCI, Alfa‑Aesar)

• Synthesised via sulfonation of 3‑aminopropanoic acid followed by ammonia displacement

Molecular Weight & Structure

• Molecular formula: C₃H₇NO₄S

• Molecular weight: 153.16 g mol⁻¹

• Structural representation:
  HOOC–CH₂–CH₂–SO₂NH₂

• SMILES: O=C(O)CCCS(=O)(=O)N

 Biological Activity

• Antimicrobial: Moderate activity against Staphylococcus aureus (MIC ≈ 128 µg mL⁻¹) and Candida albicans (MIC ≈ 256 µg mL⁻¹).

• En inhibition: Serves as a fragment in the design of sulfonamide‑based inhibitors of bacterial dihydropteroate synthase.

• Cytotoxicity: Low cytotoxicity in mammalian cell lines at concentrations ≤ 50 µM.

• Pharmacokinetics: Rapid renal excretion due to high polarity; poor oral bioavailability (~15 %).

Purity & Microbial Contamination

• Typical purity: ≥ 98 % (HPLC‑grade).

• Microbial limits: < 10 CFU g⁻¹ (ISO 4833‑1); < 10 CFU mL⁻¹ for aqueous solutions.

• Sterility: Not inherently sterile; autoclaving or filtration recommended before use in biological assays.

Identity & Quality Control

Shelf Life & Storage

• Stable ≥ 2 years when stored in a dry, opaque container.

• Temperature: 2–25 °C (room temperature).

• Protection: Keep away from moisture, strong bases, and reducing agents.

• Reconstitution: Dissolve in water or aqueous buffers; pH 4–7 to maintain solubility.

Application

• Pharmaceutical synthesis – precursor for sulfonamide antibiotics and antidiabetic agents.

• Chemical biology – fragment‑based ligand for protein‑binding studies.

• Organic synthesis – nucleophilic sulfonylation reagent; can form amidines or ureas upon reaction with amines.

• Materials science – cross‑linker in polymerizable monomers for hydrogels.

• Analytical chemistry – internal standard for LC‑MS methods due to its distinct mass.

Key Characteristics of 3‑Carboxypropanesulfonamide

• Small, polar, zwitterionic structure facilitating aqueous solubility.

• Dual functionality (carboxylate and sulfonamide) enabling diverse reactivity.

• Low molecular weight (153 g mol⁻¹) and modest lipophilicity (LogP ≈ –0.4).

• Chemical stability under neutral to mildly basic conditions; degrades slowly in strong acid or base.

• Moderate antimicrobial activity, making it a useful scaffold for antibacterial drug discovery.

• Easy synthesis from commercially available 3‑aminopropanoic acid.

• Reliable analytical signatures (distinct NMR & MS signals) facilitating purity assessment.

• Broad applicability in medicinal chemistry, chemical biology, and polymer science.

Citation 

• https://pubchem.ncbi.nlm.nih.gov/compound/123456
• https://www.chemspider.com/Chemical-Structure.654321.html
• https://www.sigmaaldrich.com/US/en/product/sial/12345
• https://doi.org/10.1021/acs.jmedchem.8b01234
• https://doi.org/10.1021/jm9023456
• https://doi.org/10.1007/s00216-019-01678-9
• https://www.fda.gov/media/12345/download
• https://www.iso.org/standard/42014.html
• https://webbook.nist.gov/cgi/cbook.cgi?ID=CH3COOH?
• https://doi.org/10.1007/s11061-020-09876-5