803529

BMPH (N-(β-maleimidopropionic acid) hydrazide, trifluoroacetic acid salt)

• Empirical Formula (Hill Notation): C₇H₉N₃O₃ · CF₃CO₂H
• Molecular Weight: 297.19
• UNSPSC Code: 12352200
• PubChem Substance ID: 329768815
• NACRES: NA.22

Properties

• Assay: ≥90%
• form: powder
• mol wt: 297.19
• reaction suitability: reagent type: cross-linking reagent
• storage condition: desiccated
• solubility: water: soluble
• functional group: hydrazide; maleimide
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: [NH3+]NC(CCN1C(C=CC1=O)=O)=O.[O-]C(C(F)(F)F)=O
• InChI: 1S/C7H9N3O3.C2HF3O2/c8-9-5(11)3-4-10-6(12)1-2-7(10)13;3-2(4,5)1(6)7/h1-2H,3-4,8H2,(H,9,11);(H,6,7)
• InChI key: BADCXPKRBUEEMA-UHFFFAOYSA-N

Description

General description

BMPH, EMCH and KMUH are heterobifunctional crosslinkers containing sulfhydryl-reactive maleimide and carbonyl-reactive hydrazide moieties. Maleimides react with free sulfhydryls (-SH) to form stable thioether 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, these crosslinkers are useful for conjugating glycoproteins and sulfhydryl-containing peptides or proteins. Alternatively, the amine of the hydrazide moiety can be reacted to carboxyl groups using the crosslinker EDC.

Features and Benefits

• Reactive groups: maleimide and hydrazide
• Reactive towards: sulfhydryl groups and carbonyl (aldehyde) groups
• Short (8.1A), sulfhydryl-to-aldehyde crosslinker with simple spacer arm (noncleavable)
• Maleimide group reacts with sulfhydryl groups to form stable thioether linkages
• 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