Disuccinimidyl glutarate Chemical Properties

Melting point:

168-172 °C

Boiling point:

485.1±55.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in dimethylsulfoxide and dimethylformamide.

form 

Solid

color 

White to Off-White

Water Solubility 

Partially soluble in water.

Sensitive 

Moisture Sensitive

BRN 

8575145

Stability:

Hygroscopic, Moisture Sensitive, Unstable in Aqueous Solution

InChI

InChI=1S/C13H14N2O8/c16-8-4-5-9(17)14(8)22-12(20)2-1-3-13(21)23-15-10(18)6-7-11(15)19/h1-7H2

InChIKey

LNQHREYHFRFJAU-UHFFFAOYSA-N

SMILES

C(ON1C(=O)CCC1=O)(=O)CCCC(ON1C(=O)CCC1=O)=O

CAS DataBase Reference

79642-50-5

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

Disuccinimidyl glutarate Usage And Synthesis

Description

Disuccinimidyl glutarate (DSG) is a homobifunctional crosslinking agent that contains amine-reactive N-hydroxysuccinimide (NHS) ester groups at each end. DSG is membrane-permeable and non-cleavable. DSG can be combined with formaldehyde fixation to improve the detection of specific protein-DNA complexes.

Chemical Properties

DSG crosslinker (Disuccinimidyl glutarate; Di(N-succinimidyl) glutarate) is a homobifunctional crosslinking reagent that is membrane permeable. DSG protein crosslinker is often used in ChIP assays to determine DNA-protein binding interactions; using DSG and formaldehyde in a two-step crosslinking strategy greatly improves the ChIP assay. Disuccinimidyl crosslinkers include disuccinimidyl glutarate (DSG), disuccinimidyl suberate (DSS), and bis-N-succinimidyl-(pentaethylene glycol) ester (BS(PEG)5)[1]. DSG crosslinking takes place through amine-reactive NHS esters at both ends of a 5-atom (7.7 angstrom) spacer arm. DSS (crosslinker arm length = 11.4Å), DSG (crosslinker arm length = 7.5Å), and disuccinimidyl tartrate (DST, crosslinker arm length = 5.8Å) are homobifunctional crosslinking reagents that react specifically with primary amines[2]. DSG crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, and then added to an aqueous crosslinking reaction. The directly water-soluble version of Di(N-succinimidyl) glutarate (DSG) is BS2G.

Characteristics

Features of disuccinimidyl glutarate:
Reactive groups: NHS ester (both ends)
Reactive towards: amino groups (primary amines)
Non-cleavable
Water-insoluble (dissolve first in DMF or DMSO)
Membrane-permeable, allowing for intracellular crosslinking
Can increase crosslinking efficiency compared to DSS in some applications

Uses

Disuccinimidyl glutarate is used as a membrane-soluble, amine-reactive N-hydroxysuccinamide ester-based homobifunctional crosslinking reagent. It is a homobifunctionla cross-linking reagent, for ex. isolation of the insulin receptor.

General Description

DSG crosslinker (Disuccinimidyl glutarate; Di(N-succinimidyl) glutarate) is a homobifunctional crosslinking reagent that is membrane permeable. DSG protein crosslinker is often used in ChIP assays to determine DNA-protein binding interactions; using DSG and formaldehyde in a two-step cross-linking strategy greatly improves the ChIP assay.
DSG crosslinking takes place through amine-reactive NHS esters at both ends of a 5-atom (7.7 angstrom) spacer arm. DSG crosslinker must be dissolved in an organic solvent, such as DMSO or DMF, then added to an aqueous crosslinking reaction. The directly water soluble version of Di(N-succinimidyl) glutarate (DSG) is BS2G.

References

[1] JeeYoung Kim, Min Park, Gun Yong Sung. “Efficient Portable Urea Biosensor Based on Urease Immobilized Membrane for Monitoring of Physiological Fluids.” Biomedicines (2020).
[2] Petr Novak. “A top-down approach to protein structure studies using chemical cross-linking and Fourier transform mass spectrometry.” European Journal of Mass Spectrometry 9 6 (2003): 623–31.

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