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Merck
CN

909688

Alkyne-A-DSBSO crosslinker

≥95%

Synonym(s):

Alkyne-tagged acid-cleavable disuccinimidyl bissulfoxide, Bis(2,5-dioxopyrrolidin-1-yl) 3,3′-((2-(but-3-yn-1-yl)-2-methyl-1,3-dioxane-5,5-diyl)bis(methylenesulfinyl))dipropionate, Mass spectrometry-cleavable crosslinker for studying protein-protein interactions

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About This Item

Empirical Formula (Hill Notation):
C25H32N2O12S2
CAS Number:
1704097-05-1
Molecular Weight:
616.66
MDL number:
MFCD32851665
UNSPSC Code:
12161502

Key Documents

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Product Name

Alkyne-A-DSBSO crosslinker, ≥95%

InChI key

CWQIIUMERHZYNI-UHFFFAOYSA-N

SMILES string

[S](=O)(CC3(COC(OC3)(CCC#C)C)C[S](=O)CCC(=O)ON2C(=O)CCC2=O)CCC(=O)ON1C(=O)CCC1=O

assay

≥95%

form

powder

availability

available only in USA

storage temp.

2-8°C

Application

Alkyne-A-DSBSO (alkyne-tagged, acid-cleavable disuccinimidyl bissulfoxide) Crosslinker is a homobifunctional, membrane-permeable, enrichable disulfoxide-containing crosslinker for analysis of protein-protein interactions (PPIs) through crosslinking mass spectrometry (XL-MS).
Alkyne-A-DSBSO possesses two N-hydroxysuccinimide (NHS) ester groups for targeting amines, a ∼14 Å spacer length, two symmetrical acid-cleavable C-S bonds, and a central bioorthogonal azide tag. After reacting with lysine (Lys) residues, the alkyne tag permits selective enrichment of crosslinked proteins or peptides with a biotin-conjugated azide probe to enhance their detection. Additionally, the post-cleavage spacer yields tagged peptides for unambiguous identification by collision-induced dissociation in tandem MS.
Alkyne-A-DSBSO Crosslinker has mapped in vivo PPIs for target protein complexes and whole proteomes from living cells. It will also be a useful proteomics tool in the quest for targeting ″undruggable″ protein targets.

Legal Information

Subject to US Patent Application #15/275,001 of the Regents of the University of California

Other Notes

Technology Spotlight: Cross-Linkers for Elucidation of Protein-Protein Interactions

Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein–protein interactions by mass spectrometry

pictograms

Flame
GHS02

signalword

Danger

hcodes

H242

Hazard Classifications

Self-react. C

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4686
MKCR1796

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Anthony M Burke et al.
Organic & biomolecular chemistry, 13(17), 5030-5037 (2015-04-01)
The cross-linking Mass Spectrometry (XL-MS) technique extracts structural information from protein complexes without requiring highly purified samples, crystallinity, or large amounts of material. However, there are challenges to applying the technique to protein complexes in vitro, and those challenges become

Articles

MS-Cleavable Cross-Linkers

Sulfoxide-containing MS-cleavable cross-linkers capture protein-protein interactions in native cellular environments, aiding PPI identification.

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