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913766

Sigma-Aldrich

9,10-Dioxo-9,10-dihydrophenanthrene-3-carboxylic acid

≥95%

Synonym(s):

9,10-phenanthrenequinone photoclick reagent, Light-initiated bioorthogonal photoclick cycloaddition reagent, PQ

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About This Item

Empirical Formula (Hill Notation):
C15H8O4
CAS Number:
32155-34-3
Molecular Weight:
252.22
MDL number:
MFCD28339454
UNSPSC Code:
12352106
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

storage temp.

−20°C

Application

9,10-Dioxo-9,10-dihydrophenanthrene-3-carboxylic acid is a photoclick reagent mediated by visible light for bioorthogonal reaction with an electron-rich vinyl either (VE) functionality (see cat#914010) for increased spatiotemporal control within biological applications. Signficantly, analysis of reactivity suggests this photoclick reaction is orthogonal to azide-alkyne and UV-mediated tetrazole-ene photoclick reactions, allowing for various means of simulteneous labeling of biomolecules in a given sample. This method requires no catalyst and is reported to be compatible with cells.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

Visible Light-Initiated Bioorthogonal Photoclick Cycloaddition

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Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Jinbo Li et al.
Journal of the American Chemical Society, 140(44), 14542-14546 (2018-10-24)
Here we report a visible light-triggered, catalyst free bioorthogonal reaction that proceeds via a distinct pathway from reported bioorthogonal reactions. The prototype of this bioorthogonal reaction was the photocycloaddition of 9,10-phenanthrenequinone with electron-rich alkenes to form fluorogenic [4+2] cycloadducts. The

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