N-tert-butyl-.beta.-acyloxycrotonamides

Woodman, D. J.; DAVIDSON, A. I.

doi:10.1021/jo00826a020

Cited by 21 publications

(7 citation statements)

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“…Mono-and diphenylacetonitrile gave ketenimines (58) and (59), respectively. and Speciale" found that reaction of chlorodiphenylacetonitrile (60) with triethyl phosphite results in formation of an N-phosphorus-substituted ketenimine(61).…”

mentioning

confidence: 99%

Synthesis and Reactions of Ketenimines

Krow¹

1971

Angew. Chem. Int. Ed. Engl.

155

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mentioning

confidence: 99%

Synthesis and Reactions of Ketenimines

Krow¹

1971

Angew. Chem. Int. Ed. Engl.

155

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“…These findings provide proof-of-principle for the notion that fairly reactive functional groups can be engineered and employed for the successful development of covalent inhibitors targeting carboxylic acids with attenuated nucleophilic potency in protein pockets. For WRK-type isoxazolium salts this fine-tuning can be achieved by varying the steric demand and electronic properties of the heterocycle substituents (Woodman and Davidson, 1970;Woodward and Woodman, 1968;. However, reactivity may also translate into selectivity.…”

Section: Discussionmentioning

confidence: 99%

Covalent Protein Labeling at Glutamic Acids

Martín‐Gago

Fansa

Winzker

et al. 2017

Cell Chemical Biology

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Covalent labeling of amino acids in proteins by reactive small molecules, in particular at cysteine SH and lysine NH groups, is a powerful approach to identify and characterize proteins and their functions. However, for the less-reactive carboxylic acids present in Asp and Glu, hardly any methodology is available. Employing the lipoprotein binding chaperone PDE6δ as an example, we demonstrate that incorporation of isoxazolium salts that resemble the structure and reactivity of Woodward's reagent K into protein ligands provides a novel method for selective covalent targeting of binding site carboxylic acids in whole proteomes. Covalent adduct formation occurs via rapid formation of enol esters and the covalent bond is stable even in the presence of strong nucleophiles. This new method promises to open up hitherto unexplored opportunities for chemical biology research.

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“…(2) (31 Wheatley4. Daly found the C = N bond length for 5 to approximate the CN triple-bond length while Wheatley found a similar CN bond length for 6.…”

Section: Rzc-cen-r T -) R;!c=c-n--rmentioning

confidence: 99%

Ketene imines

and¹,

McHenry²

Ketenes, Allenes and Related Compounds: Vol. 2 (1980)

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N-tert-butyl-.beta.-acyloxycrotonamides

Cited by 21 publications

References 0 publications

Synthesis and Reactions of Ketenimines

Synthesis and Reactions of Ketenimines

Covalent Protein Labeling at Glutamic Acids

Ketene imines

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