803480

PDPH (3-(2-pyridyldithio)propionyl hydrazide)

• Synonym(s): 3-(2-Pyridyldithio)propionate hydrazide, 3-[(2-Pyridyl)dithio]propionohydrazide
• Empirical Formula (Hill Notation): C₈N₃S₂OH₁₁
• CAS Number: 115616-51-8
• Molecular Weight: 229.32
• MDL number: MFCD00467204
• UNSPSC Code: 12352125
• PubChem Substance ID: 329768811
• NACRES: NA.22

Properties

• Assay: ≥95%
• Quality Level: 100
• form: powder
• mol wt: 229.32
• reaction suitability: reagent type: cross-linking reagent
• storage condition: desiccated
• solubility: DMSO or DMF: soluble
• functional group: hydrazide
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: NNC(CCSSC1=NC=CC=C1)=O
• InChI: 1S/C8H11N3OS2/c9-11-7(12)4-6-13-14-8-3-1-2-5-10-8/h1-3,5H,4,6,9H2,(H,11,12)
• InChI key: NITXODYAMWZEJY-UHFFFAOYSA-N

Description

General description

The PDPH is a heterobifunctional crosslinker containing sulfhydryl-reactive pyridyldithiol and carbonyl-reactive hydrazide moieties. Pyridyldithiols react with free sulfhydryls (-SH) to form disulfide bonds. Hydrazide groups react with carbonyls (aldehydes and ketones) to form stable hydrazone bonds. Aldehyde groups can be created by periodate-oxidation of sialic acid and other sugar components of glycoprotein polysaccharides. Thus, PDPH is useful for conjugating glycoproteins and sulfhydryl-containing peptides or proteins. Likewise, PDPH is useful as a sulfhydryl-addition reagent for glycoproteins and other carbohydrates; after reaction of the hydrazide to an oxidized carbohydrate, the pyridyldithiol group can be cleaved by a reducing agent to expose a sulfhydryl group. Yet another application for PDPH is to react the primary amine of the hydrazide moiety to a carboxyl group using the crosslinker EDC.

Features and Benefits

• Reactive groups: pyridyldisulfide and hydrazide
• Reactive toward: sulfhydryl groups and carbonyl (aldehyde) groups
• Short (9.2A), sulfhydryl-to-aldehyde crosslinker with disulfide bond spacer arm (cleavable)
• Pyridyldithiol group results in attachment to sulfhydryls via disulfide bond, which can be cleaved with DTT, TCEP or other reducing agents
• Hydrazide group conjugates to oxidized sugars of glycoproteins and carbohydrates
• Use sodium meta-periodate to oxidize glycosylation (e.g., sialic acid) to reactive aldehyde groups
• Use with EDC to conjugate primary amine of hydrazide group to carboxyl groups

Caution

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable