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745073

Sigma-Aldrich

N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane

for Copper-free Click Chemistry

Synonym(s):

(1α,8α,9β)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate, BCN-amine

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About This Item

Empirical Formula (Hill Notation):
C17H28N2O4
CAS Number:
1263166-93-3
Molecular Weight:
324.42
MDL number:
MFCD19705418
UNSPSC Code:
12352003
PubChem Substance ID:
329765726
NACRES:
NA.22

form

liquid

composition

carbon content, 62.94%
hydrogen content, 8.70%
nitrogen content, 8.63%

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

amine

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@]12CCC#CCC[C@]1([H])[C@@H]2COC(NCCOCCOCCN)=O

InChI

1S/C17H28N2O4/c18-7-9-21-11-12-22-10-8-19-17(20)23-13-16-14-5-3-1-2-4-6-15(14)16/h14-16H,3-13,18H2,(H,19,20)/t14-,15+,16-

InChI key

YZGOWXGENSKDSE-MUJYYYPQSA-N

Related Categories

Application

Amine functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.
N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane may be used to functionalize hyaluronic acid with bicyclo[6.1.0]nonyne (BCN) for the development of responsive HA-based physical hydrogels with tunable properties.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Comparison of strain-promoted alkyne-azide cycloaddition with established methods for conjugation of biomolecules to magnetic nanoparticles
Gruttner C, et al.
IEEE Transactions on Magnetics, 49(1), 172-176 (2013)
Folding driven self-assembly of a stimuli-responsive peptide-hyaluronan hybrid hydrogel.
Seleg?rd R, et al.
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Orientation of llama antibodies strongly increases sensitivity of biosensors
Trilling AK, et al.
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Jonas Christoffersson et al.
Biofabrication, 11(1), 015013-015013 (2018-12-14)
Liver cell culture models are attractive in both tissue engineering and for development of assays for drug toxicology research. To retain liver specific cell functions, the use of adequate cell types and culture conditions, such as a 3D orientation of
Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.
Jan Dommerholt et al.
Angewandte Chemie (International ed. in English), 49(49), 9422-9425 (2010-09-22)

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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