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744867

Sigma-Aldrich

(1R,8S,9s)-Bicyclo[6.1.0]non-4-in-9-ylmethyl]-N-succinimidylcarbonat

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

for Copper-free Click Chemistry

Synonym(e):

N-[((1R,8S,9s)-Bicyclo[6.1.0]non-4-in-9-yl)-methyloxycarbonyloxy]-succinimid, BCN-NHS, BCN-succinimidylester

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10 MG
€ 120,00
100 MG
€ 397,00

€ 120,00


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10 MG
€ 120,00
100 MG
€ 397,00

About This Item

Empirische Formel (Hill-System):
C15H17NO5
CAS-Nummer:
Molekulargewicht:
291.30
MDL-Nummer:
UNSPSC-Code:
12161502
PubChem Substanz-ID:
NACRES:
NA.22

€ 120,00


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Qualitätsniveau

Assay

>90%

Form

powder

Zusammensetzung

carbon content, 61.85%
hydrogen content, 5.88%
nitrogen content, 4.81%

Eignung der Reaktion

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

mp (Schmelzpunkt)

120  °C (248 °F)

Löslichkeit

water: insoluble

Funktionelle Gruppe

NHS ester

Lagertemp.

−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-

InChIKey

SKTDJYHCSCYLQU-ZSBIGDGJSA-N

Anwendung

Succinimidylester/NHS-funktionalisiertes Cyclooctinderivat für die Einfügung einer Cyclooctineinheit in Amin-enthaltende Verbindungen oder Biomoleküle. Cyclooctinderivate sind in durch Ringspannung geförderte kupferfreie Azid-Alkin-Cycloadditionen nützlich. Das gespannte Cyclooctin kann mit Azid-funktionalisierten Verbindungen oder Biomolekülen ohne einen Kupferkatalysator reagieren, was zu stabilen Verknüpfungen über Triazole führt.
(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]

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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?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)
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)
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)

Artikel

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.

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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