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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(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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10 MG
CN¥1,232.21
100 MG
CN¥4,888.50

CN¥1,232.21

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10 MG
CN¥1,232.21
100 MG
CN¥4,888.50

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

CN¥1,232.21

Please contact Customer Service for Availability
Request a Bulk Order

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

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-

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This Item
6317963177M9794
(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethyl N-succinimidyl carbonate for Copper-free Click Chemistry

744867

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

3-(Maleimido)propionic acid N-hydroxysuccinimide ester ≥98.5% (HPLC)

63179

3-(Maleimido)propionic acid N-hydroxysuccinimide ester

6-Maleimidohexanoic acid N-hydroxysuccinimide ester ≥98.0% (HPLC)

63177

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

6-Maleimidohexanoic acid N-hydroxysuccinimide ester ≥98%, powder

M9794

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

form

powder

form

solid

form

solid

form

powder

composition

carbon content, 61.85%

composition

-

composition

-

composition

-

functional group

NHS ester

functional group

NHS ester

functional group

NHS ester

functional group

NHS ester

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.[1]
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    BCCM9692
    BCCL6141
    BCCK8172
    BCCG4964
    BCCL0245

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