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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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Size/SKUAvailabilityPrice
10 mg
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$147.00
100 mg
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$615.00

About This Item

Empirical Formula (Hill Notation):
C15H17NO5
CAS Number:
1426827-79-3
Molecular Weight:
291.30
MDL number:
MFCD19705416
UNSPSC Code:
12161502
PubChem Substance ID:
329765714
NACRES:
NA.22
Assay:
>90%
Form:
powder

$147.00

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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

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.
(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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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This Item
742678745073
(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate for Copper-free Click Chemistry

Sigma-Aldrich

744867

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

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol for Copper-free Click Chemistry

Sigma-Aldrich

742678

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol

N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane for Copper-free Click Chemistry

Sigma-Aldrich

745073

N-[(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl]-1,8-diamino-3,6-dioxaoctane

description

for Copper-free Click Chemistry

description

for Copper-free Click Chemistry

description

for Copper-free Click Chemistry

assay

>90%

assay

-

assay

-

reaction suitability

reaction type: click chemistry, reagent type: cross-linking reagent

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

reagent type: linker, reaction type: click chemistry

Quality Level

200

Quality Level

100

Quality Level

100

solubility

water: insoluble

solubility

-

solubility

water: 1.5 g/L

form

powder

form

powder

form

liquid

mp

120  °C (248 °F)

mp

-

mp

-

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BCCM9692
    BCCN8574
    BCBM5200V
    BCBJ0789V
    BCBK9086V

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