744867

Sigma-Aldrich

(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-succinimidyl ester, BCN-NHS
Empirical Formula (Hill Notation):
C15H17NO5
CAS Number:
Molecular Weight:
291.30
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

?Click? access to multilayer functionalized Au surface: A terpyridine patterning example.
Materials Science and Engineering, C, 75, 1343-1350 (2017)
Introduction of anti-fouling coatings at the surface of supramolecular elastomeric materials via post-modification of reactive supramolecular additives
Goor OJ, et al.
Polym. Chem., 8(34), 5228-5238 (2017)
Installing an additional emission quenching pathway in the design of iridium (III)-based phosphorogenic biomaterials for bioorthogonal labelling and imaging
Li SPY, et al.
Biomaterials, 103, 305-313 (2016)
Recombinant DNA technology and click chemistry: a powerful combination for generating a hybrid elastin-like-statherin hydrogel to control calcium phosphate mineralization.
Misbah MH, et al.
Beilstein Journal of Nanotechnology, 8, 772-772 (2017)
Bio?Orthogonally Crosslinked, Engineered Protein Hydrogels with Tunable Mechanics and Biochemistry for Cell Encapsulation
Madl CM, et al.
Advances in Functional Materials, 26(21), 3612-3620 (2016)
Articles
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.
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