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761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Synonyme(s) :

DBCO-NH2, DBCO-amine

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About This Item

Formule empirique (notation de Hill):
C18H16N2O
Numéro CAS:
1255942-06-3
Poids moléculaire :
276.33
Numéro MDL:
MFCD22380759
Code UNSPSC :
12352116
ID de substance PubChem :
329766557
Nomenclature NACRES :
NA.22

Forme

solid

Capacité de réaction

reaction type: click chemistry

Pertinence de la réaction

reagent type: linker

Pf

86-96 °C

Groupe fonctionnel

amine

Température de stockage

−20°C

Chaîne SMILES 

NCCC(N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3)=O

InChI

1S/C18H16N2O/c19-12-11-18(21)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13,19H2

Clé InChI

OCCYFTDHSHTFER-UHFFFAOYSA-N

Description générale

Dibenzocyclooctyne-amine (DBCO-NH2), is a heterobifunctional linker containing a DBCO moiety commonly used for the site-specific functionalization of nanobodies, enabling the addition of reactive DBCO groups for subsequent click chemistry reactions.

Application

Dibenzocyclooctyne-amine can be used as a :
  • Linker to link azide-containing functional groups. It facilitates the formation of linkages through Strain-promoted azide-alkyne cycloaddition reactions (SPAAC)
  • Reagent in the synthesis of N-heterocyclic carbene metal thiolates. It functionalizes the metal complexes and increases their reactivity in the strain-promoted alkyne–azide cycloaddition (SPAAC) reactions
  • Amine functionalized cyclooctyne derivative. 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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

Prolonging the circulatory retention of SPIONs using dextran sulfate: in vivo tracking achieved by functionalisation with near-infrared dyes.
Abdollah MR, et al.
Faraday Discussions, 175, 41-58 (2015)
Steering the azido?tetrazole equilibrium of 4-azidopyrimidines via substituent variation?implications for drug design and azide?alkyne cycloadditions.
Thomann A, et al.
Organic & Biomolecular Chemistry, 13(43), 10620-10630 (2015)
NHC ligated group 11 metal-arylthiolates containing an azide functionality amenable to ?click? reaction chemistry
V Somasundaram, et al.
Inorganic Chemistry, 57, 11184-11192 (2018)
Strained cyclooctyne as a molecular platform for construction of multimodal imaging probes
Sun Y, et al.
Angewandte Chemie (International Edition in English), 54(20), 5981-5984 (2015)
Picomolar SARS-CoV-2 neutralization using multi-arm PEG nanobody constructs
A Moliner-Morro, et al.
Biomolecules, 10, 1661-1661 (2020)
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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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