<b>A General Synthesis of the Troponoid System Based on Solvolysis of 1,4-Dihydrobenzyl Tosylates</b>

Chapman, O. L.; Fitton, P.

doi:10.1021/ja00884a008

Cited by 49 publications

(15 citation statements)

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“…Solvolysis of 2-OBs in anhydrous acetic acid buffered with sodium acetate and in 90% dioxane-water buffered with sodium bicarbonate gave product mixtures composed ultimately of deltacyclene16 (7), and 5-deltacyclyl16 (8-), exo-2-bren-deriyl16 (9-), exo-4-brexenyl16 (10-), and 5-isodeltacyclyl17 (11-) acetates (-OAc) or alcohols (-OH), respectively. If solvolysis is interrupted prior to 100% completion, some internally returned, exo-2-brendenyl brosylate (9-OBs) can also be detected in each case.…”

Section: Resultsmentioning

confidence: 99%

Solvolysis of .beta.-(7-norbornadienyl)ethyl p-bromobenzenesulfonate. A search for unsymmetrical [20 + 20 + 1+] laticyclic stabilization

Bly¹,

Bly²,

Konizer³

et al. 1976

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

Solvolysis of .beta.-(7-norbornadienyl)ethyl p-bromobenzenesulfonate. A search for unsymmetrical [20 + 20 + 1+] laticyclic stabilization

Bly¹,

Bly²,

Konizer³

et al. 1976

J. Am. Chem. Soc.

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“…2 shows our synthesis of biotin dimedone (1), which started from the reported preparation of 1-methyl-3,5-dimethoxy-1,4-dihydrobenzoic acid (18,19) (3), which we were able to repeat with minor modifications. It was noted that the principal contaminant was the ketone from hydrolysis of one enol ether moiety; although this may be removed chromatographically (EtOAc-hexane, 2:1, v/v), the concomitant reduction in yield led us to carry on with crude 3.…”

Section: Methodsmentioning

confidence: 99%

Protein Sulfenation as a Redox Sensor

Charles

Schröder

May

et al. 2007

Molecular & Cellular Proteomics

176

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Protein sulfenic acids are reactive intermediates in the catalytic cycles of many enzymes as well as the in formation of other redox states. Sulfenic acid formation is a reversible post-translational modification with potential for protein regulation. Dimedone (5,5-dimethyl-1,3-cyclohexanedione) is commonly used in vitro to study sulfenation of purified proteins, selectively "tagging" them, allowing monitoring by mass spectrometry. However dimedone is of little use in complex protein mixtures because selective monitoring of labeling is not possible. To address this issue, we synthesized a novel biotinylated derivative of dimedone, keeping the dione cassette required for sulfenate reactivity but adding the functionality of a biotin tag. Biotin-amido(5-methyl-5-carboxamidocyclohexane 1,3-dione) tetragol (biotin dimedone) was prepared in six steps, combining 3,5-dimethoxybenzoic acid (Birch reduction, ultimately leading to the dimedone unit with a carboxylate functionality), 1-amino-11-azido-3,6,9-trioxaundecane (a differentially substituted tetragol spacer), and biotin. We loaded biotin dimedone (0.1 mM, 30 min) into rat ventricular myocytes, treated them with H 2 O 2 (0.1-10,000 M, 5 min), and monitored derivatization on Western blots using streptavidin-horseradish peroxidase. There was a dose-dependent increase in labeling of multiple proteins that was maximal at 0.1 or 1 mM H 2 O 2 and declined sharply below basal with 10 mM treatment. Cellwide labeling was observed in fixed cells probed with avidin-FITC using a confocal fluorescence microscope. Similar H 2 O 2 -induced labeling was observed in isolated rat hearts. Hearts loaded and subjected to hypoxia showed a striking loss of labeling, which returned when oxygen was resupplied, highlighting the protein sulfenates as oxygen sensors. Cardiac proteins that were sulfenated during oxidative stress were purified with avidin-agarose and identified by separation of tryptic digests by liquid chromatography with on-line analysis by mass spectrometry.

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“…Biphenyls with substituents at C-2 and C-3 tend to undergo reduction in the substituted ring (e.g. These systems do not require the presence of alcohol for reduction and it is consequently possible to alkylate the intermediate anions with alkyl halides, as (56) gives (57). Reduction of 4-methylbiphenyl is indiscriminate, however, while the 4-methoxy analog gives only deoxygenated products.…”

Section: Biphenyls Fluorenes and Fused Polycyclic Hydrocarbonsmentioning

confidence: 99%

Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

Mander

1991

Comprehensive Organic Synthesis

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A General Synthesis of the Troponoid System Based on Solvolysis of 1,4-Dihydrobenzyl Tosylates

Cited by 49 publications

References 0 publications

Solvolysis of .beta.-(7-norbornadienyl)ethyl p-bromobenzenesulfonate. A search for unsymmetrical [20 + 20 + 1+] laticyclic stabilization

Solvolysis of .beta.-(7-norbornadienyl)ethyl p-bromobenzenesulfonate. A search for unsymmetrical [20 + 20 + 1+] laticyclic stabilization

Protein Sulfenation as a Redox Sensor

Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods

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