2015
DOI: 10.1021/jacs.5b06969
|View full text |Cite
|
Sign up to set email alerts
|

A Bioorthogonal Ligation of Cyclopropenones Mediated by Triarylphosphines

Abstract: Bioorthogonal chemistries have been widely used to probe biopolymers in living systems. To date, though, only a handful of broadly useful transformations have been identified because of the stringent requirements placed on the reactants. Here we report a novel bioorthogonal ligation between cyclopropenones and functionalized phosphines. These components are stable in physiological buffers and react rapidly with one another to form covalent adducts. The cyclopropenone ligation is also distinct from other bioort… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

2
94
0
1

Year Published

2016
2016
2019
2019

Publication Types

Select...
6
1

Relationship

0
7

Authors

Journals

citations
Cited by 74 publications
(97 citation statements)
references
References 30 publications
2
94
0
1
Order By: Relevance
“…169 Lysozyme-substituted cyclopropenones were used similarly for ligation in biological systems. 169 Acetylketene 113 generated by thermolysis of the dioxinone 358 reacts with the aminoaryl podand 357 to form acetoacetanilide podand 359 (Scheme 125). 172 Such acetoacetanilidecontaining podands were then used in the Biginelli reaction as СН-active components.…”
mentioning
confidence: 99%
“…169 Lysozyme-substituted cyclopropenones were used similarly for ligation in biological systems. 169 Acetylketene 113 generated by thermolysis of the dioxinone 358 reacts with the aminoaryl podand 357 to form acetoacetanilide podand 359 (Scheme 125). 172 Such acetoacetanilidecontaining podands were then used in the Biginelli reaction as СН-active components.…”
mentioning
confidence: 99%
“…There even was a vivid description for this kind of chemical compounds: “Having a simple appearance outside, yet full of wonder inside, cyclopropenone seems like a miniature carved ivory altarpiece in a Chinese curio box.” As far as we know, cyclopropenones have been utilized as useful building blocks in transition‐metal catalysis, organocatalysis,, and cycloaddition reactions ,. These molecules could also be used as catalysts for alcohols or for bioorthogonal chemistry . With regard to organocatalytic reactions, the ring‐opening and C−C bond activation process of cyclopropenones results from either 1,2‐addition or 1,4‐addition by Lewis bases, which yielded nucleophilic intermediates and facilitated the subsequent formal [3+2] cycloaddition reations (Scheme a) ,…”
Section: Methodsmentioning
confidence: 99%
“…There still remains ad emand for further bioorthogonal reporter groups.F unctionalized cyclopropenes, [218][219][220][223][224][225][226] isonitriles, [221,227] and terminal alkenes have been introduced [216,223] which are able to undergo cycloaddition reactions with tetrazine scaffolds.R eaction partners for these scaffolds,i ncluding trans-cyclooctene,n orborene,a nd bicyclononyne,a re abiotic and stable in the cellular environment. [228,229] They react rapidly with electron-deficient tetrazines through DARinv.Asmall strained N-olefin-cyclopropenemannosamine was established as ac hemical reporter that reacted faster than strained alkenes and alkynes.A dditionally,m ethylcyclopropenes were applied in tandem with organic azides to target multiple classes of biomolecules.…”
Section: Bioorthogonal Modificationsmentioning
confidence: 99%
“…There still remains a demand for further bioorthogonal reporter groups. Functionalized cyclopropenes, isonitriles, and terminal alkenes have been introduced which are able to undergo cycloaddition reactions with tetrazine scaffolds. Reaction partners for these scaffolds, including trans ‐cyclooctene, norborene, and bicyclononyne, are abiotic and stable in the cellular environment .…”
Section: Metabolic Glycoengineering Of the N‐acyl Side Chain Of Sialmentioning
confidence: 99%