(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
Linear Formula: C₁₅H₁₇NO₅
Product Type: Chemical

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
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
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

Storage Temp.	−20°C
UNSPSC	12161502