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HomeProduct name listDisuccinimidyl glutarate

Disuccinimidyl glutarate

Synonym(s):CDHF4;desmoglein 1;DG1;DSG

Disuccinimidyl glutarate Structural

What is Disuccinimidyl glutarate?

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

The Uses of Disuccinimidyl glutarate

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.

What are the applications of Application

Disuccinimidyl glutarate is an amine-reactive, NHS ester-based crosslinker useful in 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.

Properties of Disuccinimidyl glutarate

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  DMSO (Sparingly, Sonicated), Methanol (Slightly, Sonicated)
form  Solid
color  White to Off-White
Water Solubility  Soluble in dimethylsulfoxide and dimethylformamide. 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
CAS DataBase Reference 79642-50-5

Safety information for Disuccinimidyl glutarate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Disuccinimidyl glutarate

InChIKey LNQHREYHFRFJAU-UHFFFAOYSA-N
SMILES C(ON1C(=O)CCC1=O)(=O)CCCC(ON1C(=O)CCC1=O)=O

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