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Merck

764396

Sigma-Aldrich

(E)-Cyclooct-4-enol

Sinónimos:

(4E)-4-Cycloocten-1-ol, trans-Cyclooctenol, TCO-OH, rel-(1R,4E,pR)-Cyclooct-4-enol

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About This Item

Fórmula empírica (notación de Hill):
C8H14O
Número de CAS:
Peso molecular:
126.20
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

hydroxyl

storage temp.

−20°C

SMILES string

O[C@H]1CC/C=C/CCC1

InChI

1S/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-2,8-9H,3-7H2/b2-1+/t8-/m0/s1

InChI key

UCPDHOTYYDHPEN-CMLYIYFCSA-N

Application

(E)-Cyclooct-4-enol may be used in the multi-step synthesis of trans-cyclooctene geranyl diphosphate, a novel strained-ring containing protein farnesyltransferase (PFTase) substrate that can be used in site-specific modification technologies.
Hydroxyl modified cyclooctene derivative. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.

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Referencia del producto
Descripción
Precios

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Reprint of: Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels?Alder ligation reactions.
Genady AR, et al.
Journal of Organometallic Chemistry, 798, 278-288 (2015)
Development of a novel antibody?tetrazine conjugate for bioorthogonal pretargeting.
Maggi A, et al.
Organic & Biomolecular Chemistry, 14(31), 7544-7551 (2016)
A 99mTc-Labelled Tetrazine for Bioorthogonal Chemistry. Synthesis and Biodistribution Studies with Small Molecule trans-Cyclooctene Derivatives.
Vito A, et al.
PLoS ONE, 11(12), e0167425-e0167425 (2016)
Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels?Alder ligation reactions.
Genady AR, et al.
Journal of Organometallic Chemistry, 791, 204-213 (2015)
Site?Specific Labeling of Proteins and Peptides with Trans?cyclooctene Containing Handles Capable of Tetrazine Ligation
Wollack JW, et al.
Chemical Biology & Drug Design, 84(2), 140-147 (2014)

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