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803529

Sigma-Aldrich

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

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About This Item

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

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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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