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914010

Sigma-Aldrich

4-Nitrophenyl (2-(vinyloxy)ethyl) carbonate

≥95%

Synonym(s):

Light-initiated bioorthogonal photoclick cycloaddition reagent, VE, Vinyl ether photoclick reagent

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About This Item

Empirical Formula (Hill Notation):
C11H11NO6
CAS Number:
2257426-02-9
Molecular Weight:
253.21
UNSPSC Code:
12352200

Assay

≥95%

form

liquid

storage temp.

−20°C

Application

4-Nitrophenyl (2-(vinyloxy)ethyl) carbonate is a vinyl ether photoclick reagent (VE) mediated by visible light for bioorthogonal reaction with a 9,10-phenanthrenequinone (PQ) photoclick reagent (see cat# 913766) 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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Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

914010-BULK:
914010-VAR:
914010-100MG:

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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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