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EMCH


A mid-length crosslinker for conjugating glycoprotein carbohydrates to sulfhydryl groups.

Pierce EMCH

Thermo Scientific Pierce EMCH is a mid-length, maleimide-and-hydrazide crosslinker for conjugating sulfhydryls (cysteines) to carbonyls (aldehyde or ketones, such as those formed by oxidation of glycoprotein carbohydrates).

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.

Highlights:

  • Reactive groups: maleimide and hydrazide
  • Reactive towards: sulfhydryl groups and carbonyl (aldehyde) groups
  • Mid-length (11.8A), 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

Applications:

  • Chemical crosslinking of glycoproteins to sulfhydryl-containing molecules
  • Use with EDC for reactivity toward carboxyl groups

Product Details:

N-epsilon-Maleimidocaproic acid hydrazide-TFA; EMCH
 
Chemical structure of EMCH crosslinking reagent.

 

Properties of EMCH.
Molecular formula C10H15N3O3
Molecular weight 225.24
Spacer arm length 11.8 Å (6 atoms)
Storage conditions 4°C, protect from moisture, use only fresh solutions
Reactive groups: Maleimide, reacts with sulfhydryls at pH 6.5-7.5
  Hydrazide, reacts with carbonyls at pH 5.5-7.5

Specifications of EMCH:

We manufacture EMCH to the highest specifications to produce the most specific bioconjugates, ensure the integrity of your data and to provide you with the highest degree of consistency. Each lot of EMCH is tested to meet the following minimum specifications.

  • NMR purity: >90%
  • Melting point: 99-110°C
  • Identity: IR scan shows only peaks characteristic of the structure and functional groups of EMCH

References:

  1. Trail, P.A., et al. (1993). Science 261, 212-215.

Product References:

Crosslinker Application Guide -- search for recent literature references for this product

Related Resources:

Overview of crosslinking
Chemistry of crosslinking
Protein glycosylation technical guide

Related Products:

Crosslinkers at a glance (selection guide)


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
22106 EMCH
Formulation: N-epsilon-Maleimidocaproic acid hydrazide-TFA; solid
Sufficient For: 147mL of typical 1X (1mM) reaction solution, or approx. 25 uses at 2mg reagent per use
50mg Product Instructions for product #22106 EMCH MSDS for product #22106 EMCH Certificate of Analysis for product #22106 EMCH $175.00

Add to cart
22106B EMCH
Formulation: N-epsilon-Maleimidocaproic acid hydrazide-TFA; solid
Custom MSDS for product #22106B EMCH Certificate of Analysis for product #22106B EMCH

Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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