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803219

Sigma-Aldrich

Sulfo-EGS (ethylene glycol bis(sulfosuccinimidyl succinate))

Synonym(s):

Ethylene glycolbis(sulfosuccinimidylsuccinate), bis(sulfosuccinimidyl) 4,4′-[(ethylene)dioxy]bis(4-oxobutanoate)

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About This Item

Empirical Formula (Hill Notation):
C18H18O18N2Na2S2
CAS Number:
Molecular Weight:
660.45
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

mol wt

660.45

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

water: soluble

shipped in

ambient

storage temp.

−20°C

InChI

1S/C18H20N2O18S2.2Na/c21-11-7-9(39(29,30)31)17(27)19(11)37-15(25)3-1-13(23)35-5-6-36-14(24)2-4-16(26)38-20-12(22)8-10(18(20)28)40(32,33)34;;/h9-10H,1-8H2,(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2

InChI key

IYBKWXQWKPSYDT-UHFFFAOYSA-L

General description

EGS is a water-insoluble, homobifunctional N-hydroxysuccinimide ester (NHS ester) and Sulfo-EGS is its water-soluble analog. The spacer arm contains two cleavable ester sites that may be broken with hydroxylamine, which yields two fragments with terminal amide bonds and the release of ethylene glycol. These reagents are often used for conjugating radiolabeled ligands to cell surface receptors. The water insoluble reagent EGS does not possess a charged group, is lipophilic and, therefore, membrane-permeable and useful for intracellular and intramembrane protein conjugation. EGS is first dissolved in DMSO or DMF and added to the aqueous reaction mixture at a final solvent concentration of 10-20%, to minimize detrimental affects to the protein.

Features and Benefits

  • Reactive groups: sulfo-NHS ester (both ends)
  • Reactive towards: amino groups (primary amines)
  • Water-soluble; compare to EGS
  • Membrane-impermeable, allowing for cell surface labeling
  • Crosslinks formed are reversible at pH 8.5 using hydroxylamine for 3 to 6 hours at 37°C
  • Lactose dehydrogenase retained 60% of its activity after reversible crosslinking with EGS

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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