744867

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

for Copper-free Click Chemistry

• 동의어(들): N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester
• 실험식(Hill 표기법): C₁₅H₁₇NO₅
• CAS Number: 1426827-79-3
• Molecular Weight: 291.30
• MDL number: MFCD19705416
• UNSPSC 코드: 12161502
• PubChem Substance ID: 329765714
• NACRES: NA.22

속성

• 분석: >90%
• 양식: powder
• 구성: carbon content, 61.85% ; hydrogen content, 5.88% ; nitrogen content, 4.81%
• 반응 적합성: reaction type: click chemistry; reagent type: cross-linking reagent
• mp: 120 °C (248 °F)
• solubility: water: insoluble
• 작용기: NHS ester
• 저장 온도: −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-
• InChI key: SKTDJYHCSCYLQU-ZSBIGDGJSA-N

설명

애플리케이션

(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.

포장

Bottomless glass bottle. Contents are inside inserted fused cone.

안전성 정보

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable