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

ALDRICH/744867 - for Copper-free Click Chemistry

Synonym: N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide; BCN-NHS; BCN-succinimidyl ester

CAS Number: 1426827-79-3
Empirical Formula (Hill Notation): C15H17NO5
Molecular Weight: 291.30
MDL Number: MFCD19705416
Linear Formula: C15H17NO5
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-744867-10MG 10 mg
 $140.00
1/EA		 Add To Favorites
45-744867-100MG 100 mg
 $586.00
1/EA		 Add To Favorites

 

assay >90%
composition carbon content, 61.85%
  hydrogen content, 5.88%
  nitrogen content, 4.81%
form powder
functional group NHS ester
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
mp 120  °C (248 °F)
Quality Level 200 
reaction suitability reaction type: click chemistry
  reagent type: cross-linking reagent
SMILES string [H][C@@]12CCC#CCC[C@]1([H])[C@@H]2COC(ON3C(CCC3=O)=O)=O
solubility water: insoluble
storage temp. −20°C
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.
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.
Packaging: Bottomless glass bottle. Contents are inside inserted fused cone.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity >90%
mp 120  °C (248 °F)
Storage Temp. −20°C
UNSPSC 12161502

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