744867

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

for Copper-free Click Chemistry

• Synonim(y): N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester
• Wzór empiryczny (zapis Hilla): C₁₅H₁₇NO₅
• Numer CAS: 1426827-79-3
• Masa cząsteczkowa: 291.30
• MDL number: MFCD19705416
• UNSPSC Code: 12161502
• PubChem Substance ID: 329765714
• NACRES: NA.22
• Assay: >90%
• Form: powder

Właściwości

• Quality Segment: 200
• assay: >90%
• form: powder
• composition: carbon content, 61.85% , hydrogen content, 5.88% , nitrogen content, 4.81%
• reaction suitability: reaction type: click chemistry, reagent type: cross-linking reagent
• technique(s): targeted protein degradation: suitable
• mp: 120 °C (248 °F)
• solubility: water: insoluble
• functional group: NHS ester
• storage temp.: −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

Opis

Application

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.

(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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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Informacja o środkach bezpieczeństwa

• Klasa składowania: 11 - Combustible Solids
• Co się dzieje?: WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable