744867

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

for Copper-free Click Chemistry

• Synonyme(s) : N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester
• Formule empirique (notation de Hill) : C₁₅H₁₇NO₅
• Numéro CAS: 1426827-79-3
• Poids moléculaire : 291.30
• Numéro MDL: MFCD19705416
• Code UNSPSC : 12161502
• ID de substance PubChem : 329765714
• Nomenclature NACRES : NA.22

Propriétés

• Essai: >90%
• Forme: powder
• Composition: carbon content, 61.85% ; hydrogen content, 5.88% ; nitrogen content, 4.81%
• Capacité de réaction: reaction type: click chemistry
• Pertinence de la réaction: reagent type: cross-linking reagent
• Pf: 120 °C (248 °F)
• Solubilité: water: insoluble
• Groupe fonctionnel: NHS ester
• Température de stockage: −20°C
• Chaîne 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-
• Clé InChI: SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Description

Application

(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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable