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744867

Sigma-Aldrich

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate

for Copper-free Click Chemistry

Sinonimo/i:

N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester

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About This Item

Formula empirica (notazione di Hill):
C15H17NO5
Numero CAS:
1426827-79-3
Peso molecolare:
291.30
Codice UNSPSC:
12161502
ID PubChem:
329765714
NACRES:
NA.22

Livello qualitativo

200

Forma fisica

powder

Composizione

carbon content, 61.85%
hydrogen content, 5.88%
nitrogen content, 4.81%

Impiego in reazioni chimiche

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

Gruppo funzionale

NHS ester

Temperatura di conservazione

−20°C

Stringa SMILE

[H][C@@]12CCC#CCC[C@]1([H])[C@@H]2COC(ON3C(CCC3=O)=O)=O

InChI

1S/C15H17NO5/c17-13-7-8-14(18)16(13)21-15(19)20-9-12-10-5-3-1-2-4-6-11(10)12/h10-12H,3-9H2/t10-,11+,12-
SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Applicazioni

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate may be used to functionalize the primary amines of the lysine residue of recombinant elastin-like proteins (ELPs). These functionalized ELPs quickly undergo cross-linking via bio-orthogonal strain-promoted azide-alkyne cycloaddition reactions to form hydrogels with high gelation kinetics and tunable mechanics, making them useful biomaterials for cell encapsulation.{67
It may also be used to synthesize bicyclononyne functionalized poly(ethylene glycol) polymer coatings with anti-fouling properties towards protein adhesion and cell adhesion for supramolecular ureidopyrimidinone (UPy) based materials.
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 strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG8596
BCCG4964
BCCG1713
BCCF9008
BCCF2905

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Dibenzocyclooctyne-PEG4-acid for Copper-free Click Chemistry

Sigma-Aldrich

759902

Dibenzocyclooctyne-PEG4-acid

Installing an additional emission quenching pathway in the design of iridium (III)-based phosphorogenic biomaterials for bioorthogonal labelling and imaging
Li SPY, et al.
Biomaterials, 103, 305-313 (2016)
Improved positron emission tomography imaging of glioblastoma cancer using novel 68Ga-labeled peptides targeting the urokinase-type plasminogen activator receptor (uPAR).
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Amino Acids, 49(6), 1089-1100 (2017)
Bio?Orthogonally Crosslinked, Engineered Protein Hydrogels with Tunable Mechanics and Biochemistry for Cell Encapsulation
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Recombinant DNA technology and click chemistry: a powerful combination for generating a hybrid elastin-like-statherin hydrogel to control calcium phosphate mineralization.
Misbah MH, et al.
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?Click? access to multilayer functionalized Au surface: A terpyridine patterning example.
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Articoli

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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