744867

(1R,8S,9s)-Bicyclo[6.1.0]non-4-in-9-ylmethyl]-N-succinimidylcarbonat

for Copper-free Click Chemistry

• Synonym(e): N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-in-9-yl)-methyloxycarbonyloxy]-succinimid, BCN-NHS, BCN-succinimidylester
• Empirische Formel (Hill-System): C₁₅H₁₇NO₅
• CAS-Nummer: 1426827-79-3
• Molekulargewicht: 291.30
• UNSPSC-Code: 12161502
• PubChem Substanz-ID: 329765714
• NACRES: NA.22

Eigenschaften

• Form: powder
• Zusammensetzung: carbon content, 61.85% ; hydrogen content, 5.88% ; nitrogen content, 4.81%
• Eignung der Reaktion: reaction type: click chemistry; reagent type: cross-linking reagent
• Funktionelle Gruppe: NHS ester
• Lagertemp.: −20°C
• SMILES String: [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-
• InChIKey: SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Beschreibung

Anwendung

Succinimidylester/NHS-funktionalisiertes Cyclooctinderivat für die Einfügung einer Cyclooctineinheit in Amin-enthaltende Verbindungen oder Biomoleküle. Cyclooctinderivate sind in durch Ringspannung geförderte kupferfreie Azid-Alkin-Cycloadditionen nützlich. Das gespannte Cyclooctin kann mit Azid-funktionalisierten Verbindungen oder Biomolekülen ohne einen Kupferkatalysator reagieren, was zu stabilen Verknüpfungen über Triazole führt.

(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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable