Disuccinimidyl suberate

Disuccinimidyl suberate[1]
Names
Preferred IUPAC name
Bis(2,5-dioxopyrrolidin-1-yl) octanedioate
Other names
DSS; Suberic acid bis(N-hydroxysuccinimide ester)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.130.330 Edit this at Wikidata
UNII
  • InChI=1S/C16H20N2O8/c19-11-7-8-12(20)17(11)25-15(23)5-3-1-2-4-6-16(24)26-18-13(21)9-10-14(18)22/h1-10H2 ☒N
    Key: ZWIBGKZDAWNIFC-UHFFFAOYSA-N ☒N
  • C1CC(=O)N(C1=O)OC(=O)CCCCCCC(=O)ON2C(=O)CCC2=O
Properties
C16H20N2O8
Molar mass 368.342 g·mol−1
Appearance Solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Disuccinimidyl suberate (DSS) is a six-carbon lysine-reactive non-cleavable cross-linking agent.

It consists of functional groups It is a homobifunctional N-hydroxysuccinimide (NHS) ester formed by carbodiimide-activation of carboxylate molecules, with identical reactive groups at either end.[2] The reactive groups are separated by a spacer and in this molecule it is a six carbon alkyl chain.[3] This reagent is mainly used to form intramolecular crosslinks and preparation of polymers from monomers. It is ideal for receptor ligand cross-linking.

DSS is reactive towards amine groups (primary amines) at pH 7.0-9.0. It is membrane permeable, therefore permitting intracellular cross-linking, has high purity, is non-cleavable, and is water-insoluble (it must be dissolved in a polar organic solvent such as DMF or DMSO before addition to sample.)[4]

Its reaction specificity, reaction product stability, and lack of reaction by-products make it a commonly used cross-linking agent.[3]

  1. ^ Suberic acid bis(N-hydroxysuccinimide ester) at Sigma-Aldrich
  2. ^ Crosslinking Reagents Handbook (PDF). Thermo Fisher Scientific. 2012.
  3. ^ a b Belsom A, Rappsilber J (February 2021). "Anatomy of a crosslinker". Current Opinion in Chemical Biology. Omics. 60: 39–46. doi:10.1016/j.cbpa.2020.07.008. hdl:20.500.11820/7655d96c-59ea-43da-96b1-fdce03f2ae84. PMID 32829152.
  4. ^ Leitner A, Walzthoeni T, Kahraman A, Herzog F, Rinner O, Beck M, Aebersold R (August 2010). "Probing native protein structures by chemical cross-linking, mass spectrometry, and bioinformatics". Molecular & Cellular Proteomics. 9 (8): 1634–1649. doi:10.1074/mcp.R000001-MCP201. PMC 2938055. PMID 20360032.