3-(1-Pyridinio)-1-propanesulfonate
[CAS# 15471-17-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 3-(1-Pyridinio)-1-propanesulfonate
• Synonyms: 1-(3-Sulphonatopropyl)pyridinium; 1,3-Sulfopropyl pyridinium hydroxide inner salt; Sulfopropylpyridiniumhydroxideinner salt; PPS
• Molecular Formula: C₈H₁₁NO₃S
• Molecular Weight: 201.24
• CAS Registry Number: 15471-17-7
• EC Number: 239-491-3
• SMILES: C1=CC=[N+](C=C1)CCCS(=O)(=O)[O-]

Properties

• Melting point: 280 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

3-(1-Pyridinio)-1-propanesulfonate, commonly known as PPS, is a zwitterionic compound that has found significant use in biochemistry and pharmaceutical applications due to its unique chemical structure. This compound consists of a pyridinium group connected to a propanesulfonate moiety, which imparts a balanced combination of positive and negative charges, making it electrically neutral overall. The discovery and subsequent development of PPS were driven by the need for biocompatible and inert molecules that could function as stabilizing agents, particularly in protein and enzyme solutions.

PPS was initially explored for its stabilizing properties in enzyme formulations. Due to its zwitterionic nature, PPS effectively reduces protein aggregation and maintains enzyme activity by providing a balanced ionic environment. This property has made it a valuable additive in the pharmaceutical industry, where protein-based drugs and enzymes are often sensitive to denaturation or aggregation under storage and transport conditions. By interacting with proteins in solution without causing destabilization, PPS enhances the stability of these biologically active molecules, extending their shelf life and preserving their therapeutic efficacy.

In addition to its role as a stabilizer, 3-(1-Pyridinio)-1-propanesulfonate has also been employed in buffer solutions, particularly in biochemical research. Its zwitterionic properties make it a useful buffer component, capable of maintaining a stable pH in various biochemical reactions. The neutral charge of PPS allows it to interact minimally with other charged species in the reaction medium, ensuring that it does not interfere with the biological processes being studied. This makes it a preferred choice in sensitive assays where non-reactivity and biocompatibility are critical.

The non-toxic nature of PPS has also contributed to its popularity in biomedical applications. Studies have shown that PPS does not exhibit significant cytotoxicity, making it suitable for use in cell culture media and other biological systems. Its ability to prevent unwanted interactions between biomolecules while maintaining their functional integrity has broadened its utility across multiple fields, including drug formulation, enzyme preservation, and diagnostic assays.

References

2016. Activity-stability relationships revisited in blue oxidases catalyzing electron transfer at extreme temperatures. Extremophiles : life under extreme conditions, 20, 6.
DOI: 10.1007/s00792-016-0851-9

2017. Differential Precipitation and Solubilization of Proteins. Methods in molecular biology (Clifton, N.J.), 1485.
DOI: 10.1007/978-1-4939-6412-3_10

2023. Protein Extraction and Purification by Differential Solubilization. Methods in molecular biology (Clifton, N.J.), 2628.
DOI: 10.1007/978-1-0716-3362-5_17