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761532

Sigma-Aldrich

Dibenzocyclooctyne-S-S-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

DBCO-S-S-NHS ester, DBCO-S-S-SE, DBCO-S-S-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C28H27N3O6S2
Molecular Weight:
565.66
MDL number:
MFCD22380758
UNSPSC Code:
12352200
PubChem Substance ID:
329766556
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

mp

192-197 °C

storage temp.

−20°C

SMILES string

O=C(CCC(NCCSSCCC(ON(C(CC1)=O)C1=O)=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C28H27N3O6S2/c32-24(29-16-18-39-38-17-15-28(36)37-31-26(34)13-14-27(31)35)11-12-25(33)30-19-22-7-2-1-5-20(22)9-10-21-6-3-4-8-23(21)30/h1-8H,11-19H2,(H,29,32)

InChI key

RPNGUSKTYYIUDE-UHFFFAOYSA-N

Application

Cleavable succinimidyl ester/NHS functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage. The disulfide present can be readily cleaved using mild reducing conditions (10-50 mM DTT at 37°C for 30 min or 5% ß-mercaptoethanol in SDS-PAGE sample buffer at 100°C for 5 minutes).

Caution: Please avoid reducing agents and amine or azide containing buffers during coupling/labeling reactions. Only use reducing agents when cleavage of the disulfide is desired.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV1674V
MKBK9318

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Julius Wiener et al.
Scientific reports, 10(1), 1457-1457 (2020-01-31)
Oligonucleotide-conjugated antibodies have gained importance for their use in protein diagnostics. The possibility to transfer the readout signal from the protein to the DNA level with an oligonucleotide-conjugated antibody increased the sensitivity of protein assays by orders of magnitude and
Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.
Xinghai Ning et al.
Angewandte Chemie (International ed. in English), 47(12), 2253-2255 (2008-02-16)
Nicholas J Agard et al.
ACS chemical biology, 1(10), 644-648 (2006-12-19)
Detection of metabolites and post-translational modifications can be achieved using the azide as a bioorthogonal chemical reporter. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly
Jeremy M Baskin et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(43), 16793-16797 (2007-10-19)
Dynamic imaging of proteins in live cells is routinely performed by using genetically encoded reporters, an approach that cannot be extended to other classes of biomolecules such as glycans and lipids. Here, we report a Cu-free variant of click chemistry
John C Jewett et al.
Journal of the American Chemical Society, 132(11), 3688-3690 (2010-03-02)
Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole

Articles

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

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