3-(2-Pyridyldithio)-propionic acid-OSu is an amino acid derivative in which a propionic acid framework is functionalized as an N-hydroxysuccinimide (OSu) ester, and the side chain bears a 2-pyridyldithio (pyridyl disulfide) group that can participate in disulfide exchange chemistry. The molecule contains a carboxylic acid functionality masked as an OSu ester for acyl transfer, along with the pyridyl-disulfide moiety that provides a redox-active sulfur handle and a leaving group associated with the pyridine ring during exchange. In research and synthetic workflows, this electrophilic OSu ester is used as an activated carboxyl precursor for forming amide linkages with nucleophiles (e.g., amines) while the pyridyldithio group provides a chemical handle for preparing disulfide-containing conjugates or for subsequent thiol/disulfide manipulation in bioconjugation and labeling strategies.
CAT No: CP27357
CAS No:68181-17-9
Synonyms/Alias:SPDP;68181-17-9;N-Succinimidyl3-(2-pyridyldithio)propionate;3-(2-Pyridyldithio)propionicacidN-hydroxysuccinimideester;3-(2-Pyridyldithio)propionicAcidN-SuccinimidylEster;NSC677449;Succinimidyl3-(2-pyridyldithio)propionate;(2,5-dioxopyrrolidin-1-yl)3-(2-pyridyldisulfanyl)propanoate;2,5-dioxopyrrolidin-1-yl3-(pyridin-2-yldisulfanyl)propanoate;SPDPCrosslinker;SCHEMBL42368;P3415_SIGMA;AC1L2P93;CTK8B3905;MolPort-003-850-066;EINECS269-034-3;ANW-43417;NSC344485;ZINC71788592;AKOS015898576;NSC-344485;3-(2-Pyridyldithio)-propionicacid-osu;AN-16618;BP-22650;HE006390
3-(2-Pyridyldithio)-propionic acid-OSu is a thiol-reactive amino acid derivative built around an N-hydroxysuccinimide (OSu) ester motif, enabling efficient acyl transfer to primary amines under standard bioconjugation conditions. The side-chain contains a 2-pyridyldithio group that serves as a disulfide-forming handle for subsequent thiol exchange, which is commonly leveraged to generate stable thioether or disulfide-linked products depending on the downstream nucleophile. This reagent is frequently used in chemical biology and biomaterials workflows where controlled introduction of a thiol-reactive functionality is required for protein labeling, linker installation, or surface functionalization.
1. Protein Amine Labeling
3-(2-Pyridyldithio)-propionic acid-OSu is used by protein chemistry and chemical biology groups to install a 2-pyridyldithio-containing acyl functionality onto lysine residues or other accessible primary amines. The OSu ester design supports straightforward coupling workflows to prepare labeled proteins, antibody conjugates, or enzyme conjugates for downstream assays and mechanistic studies. Researchers select this derivative when they want an amine-reactive handle that can later participate in thiol-disulfide exchange chemistry, enabling stepwise construction of conjugates with defined connectivity.
2. Thiol-Disulfide Linker Installation
3-(2-Pyridyldithio)-propionic acid-OSu is applied as a linker-building reagent to introduce a pyridyldithio group that can be converted into reactive disulfide intermediates for subsequent coupling to thiol-containing biomolecules. In bioconjugation development, this supports modular assembly strategies where an amine-functionalized carrier is first modified, then reacted with a thiol-bearing partner such as a cysteine-terminated peptide, a thiolated oligonucleotide, or a thiol-functional polymer. The 2-pyridyldithio moiety is particularly valued for workflows that benefit from thiol exchange to tune conjugate architecture and attachment chemistry.
3. Biomaterial Surface Functionalization
3-(2-Pyridyldithio)-propionic acid-OSu is used in biomaterials and surface chemistry to functionalize amine-bearing surfaces and coatings with a thiol-reactive disulfide handle. Material developers employ it to create reactive linkers on polymers, hydrogel matrices, or protein-coated substrates, enabling later immobilization of thiol-containing ligands, capture reagents, or bioactive peptides. This application is driven by the combination of an OSu ester for efficient surface amine coupling and the pyridyldithio group for subsequent thiol-based attachment steps that are compatible with many lab-scale fabrication and characterization workflows.
4. Peptide and Biomolecule Conjugation
3-(2-Pyridyldithio)-propionic acid-OSu supports peptide chemistry and conjugation workflows where a thiol-reactive linkage is required after initial amine coupling. Peptide and reagent developers use the OSu ester to attach the pyridyldithio-containing acyl group to amine-bearing peptides or peptide carriers, then use the resulting disulfide-forming functionality to connect to thiol-containing partners. This approach is commonly used when a two-step conjugation strategy is preferred to manage coupling order, improve labeling control, or generate conjugates with a specific chemical connectivity for analytical characterization and downstream chemical biology experiments.
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