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  • 744867 - (1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate

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744867 Sigma-Aldrich

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

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 1516551-46-4

  • Empirical Formula (Hill Notation) C15H17NO5

  • Molecular Weight 291.30

  •  PubChem Substance ID 329765714

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry, Crosslinkers,
Quality Level   100
composition   carbon content, 61.85%
  hydrogen content, 5.88%
  nitrogen content, 4.81%
reaction suitability   reaction type: click chemistry
  reagent type: cross-linking reagent
storage temp.   −20°C
SMILES string   O=C(OCC1[C@@H]2CCC#CCC[C@H]12)ON3C(=O)CCC3=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

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.

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.1 The absence of exogenous me...
Keywords: 1,3-Dipolar cycloaddition, Catalysis, Click chemistry, Cycloadditions, Pharmaceutical, Positron Emission Tomography

Peer-Reviewed Papers
15

References

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