744867

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

for Copper-free Click Chemistry

• Sinónimos: N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester
• Fórmula empírica (notación de Hill): C₁₅H₁₇NO₅
• Número de CAS: 1426827-79-3
• Peso molecular: 291.30
• Número MDL: MFCD19705416
• Código UNSPSC: 12161502
• ID de la sustancia en PubChem: 329765714
• NACRES: NA.22

Propiedades

• Ensayo: >90%
• Formulario: powder
• composición: carbon content, 61.85% ; hydrogen content, 5.88% ; nitrogen content, 4.81%
• idoneidad de la reacción: reaction type: click chemistry; reagent type: cross-linking reagent
• mp: 120 °C (248 °F)
• solubilidad: water: insoluble
• grupo funcional: NHS ester
• temp. de almacenamiento: −20°C
• cadena SMILES: [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-
• Clave InChI: SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Descripción

Aplicación

(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.[1]

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.

Envase

Bottomless glass bottle. Contents are inside inserted fused cone.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable