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Merck
모든 사진(3)

주요 문서

761540

Sigma-Aldrich

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

동의어(들):

DBCO-NH2, DBCO-amine

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About This Item

실험식(Hill 표기법):
C18H16N2O
CAS Number:
Molecular Weight:
276.33
MDL number:
UNSPSC 코드:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

양식

solid

반응 적합성

reaction type: click chemistry
reagent type: linker

mp

86-96 °C

작용기

amine

저장 온도

−20°C

SMILES string

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

InChI key

OCCYFTDHSHTFER-UHFFFAOYSA-N

일반 설명

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.

애플리케이션

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable


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문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

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)
An azide functionalized oligothiophene ligand?A versatile tool for multimodal detection of disease associated protein aggregates.
Johansson LB, et al.
Biosensors And Bioelectronics, 63, 204-211 (2015)
Covalently linking CuInS 2 quantum dots with a Re catalyst by click reaction for photocatalytic CO 2 reduction
J Huang, et al.
Dalton Transactions, 47, 10775-10783 (2018)
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)
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)

문서

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.

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

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