Sulfo-LC-SPDP

Key facts

CAS number

169751-10-4

Purity

>90%

Form

Solid

form

Molecular weight

527.6 Da

Molecular formula

C₁₈H₂₂N₃NaO₈S₃

PubChem

4588467

Nature

Synthetic

Solubility

Soluble in water to 10 mM

Biochemical name

Sulfo-N-succinimidyl 6-[3-(2-Pyridyldithio)propionamido] Hexanoate, Sodium Salt

Biological description

Sulfo-LC-SPDP releases a byproduct, pyridine-2-thione after reacting with free sulfhydryl groups. By measuring the release of this byproduct at 343 nm, the reaction can be easily followed.

Amine-reactive; the "long chain" Sulfo-LC-SPDP crosslinking reagent has a 15.7 Å spacer arm.

More water-soluble than the corresponding LC-SPDP.

Membrane-impermeable which enables crosslinking on cell surface.

The cleavable spacer arm enables separation of cross-linked products.

APPLICATIONS:

Reversible crosslinking of proteins.

N-hydroxysulfosuccinimide (Sulfo-NHS) ester that reacts with primary amines, as found in lysine side chains.

Sulfo-LC-SPDP crosslinking molecule pyridinyldisulfide reacts with sulhydryls to yield a reversible disulfide bond.

Canonical smiles

C1C(C(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCSSC2=CC=CC=N2)S(=O)(=O)[O-].[Na+]

InChi

InChI=1S/C18H23N3O8S3.Na/c22-14(8-11-30-31-15-6-3-5-10-20-15)19-9-4-1-2-7-17(24)29-21-16(23)12-13(18(21)25)32(26,27)28;/h3,5-6,10,13H,1-2,4,7-9,11-12H2,(H,19,22)(H,26,27,28);/q;+1/p-1

InChiKey

ZAPNXDUFCQIHFS-UHFFFAOYSA-M

IUPAC Name

sodium;2,5-dioxo-1-[6-[3-(pyridin-2-yldisulfanyl)propanoylamino]hexanoyloxy]pyrrolidine-3-sulfonate