803677
EMCH (N-(ε-maleimidocaproic acid) hydrazide, trifluoroacetic acid salt)
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About This Item
Empirical Formula (Hill Notation):
C10H15N3O3 · CF3CO2H
Molecular Weight:
339.27
MDL number:
UNSPSC Code:
12352125
PubChem Substance ID:
NACRES:
NA.22
Assay:
≥90%
Form:
powder
SMILES string
O=C(C=CC1=O)N1CCCCCC(N[NH3+])=O.[O-]C(C(F)(F)F)=O
InChI
1S/C10H15N3O3.C2HF3O2/c11-12-8(14)4-2-1-3-7-13-9(15)5-6-10(13)16;3-2(4,5)1(6)7/h5-6H,1-4,7,11H2,(H,12,14);(H,6,7)
InChI key
DRURMGRBAVYWCL-UHFFFAOYSA-N
assay
≥90%
form
powder
mol wt
339.27
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
Quality Level
Related Categories
General description
3,3′-N-[ε-Maleimidocaproic acid] hydrazide, trifluoroacetic acid salt (EMCH) is a water-soluble, heterobifunctional, membrane permeable crosslinker. It contains a sulfhydryl reactive maleimide group and carbonyl reactive hydrazide group at each end of a 6-carbon spacer arm. Maleimides react with sulfhydryls at pH 6.5-7.5 to form stable thiol ether bonds, along with release of the maleimide leaving group. Proteins with cysteine residues not involved in disulfide bond formation are targets for maleimide reactive groups. Carbonyl groups, whilst not found naturally on proteins can be formed by ring sugar reduction to form aldehydes which react with hydrazides at pH5.5-7.5.
Features and Benefits
- Reactive groups: maleimide and hydrazide
- Reactive towards: sulfhydryl groups and carbonyl (aldehyde) groups
- Mid-length (11.8Å), 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
Disclaimer
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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