744867
(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate
for Copper-free Click Chemistry
Synonym(s):
N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-yl)methyloxycarbonyloxy]succinimide, BCN-NHS, BCN-succinimidyl ester
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About This Item
Empirical Formula (Hill Notation):
C15H17NO5
CAS Number:
Molecular Weight:
291.30
MDL number:
UNSPSC Code:
12161502
PubChem Substance ID:
NACRES:
NA.22
Assay:
>90%
Form:
powder
Quality Segment
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
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.
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.
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.
Storage Class
11 - Combustible Solids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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