A Facile Oxidation and Oxygen Insertion of the Cyclopentadiene Ring by Molecular Oxygen in Solution

Gong, Weitao; Ning, Guiling; Li, Xincheng; Wang, Li; Yuan, Lin

doi:10.1021/jo050715q

Cited by 19 publications

(10 citation statements)

References 42 publications

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“…The appropriate number and type of substituents on the ring should be maintained to retain the reactivity of pyrylium salts. With these criteria in mind, we designed and synthesized nine pyrylium salts as precious reports − (Figure ).…”

Section: Resultsmentioning

confidence: 99%

α-Active Pyrylium Salt 2,4,5-Triphenylpyrylium for Improved Mass Spectrometry-Based Detection of Peptides

Huang

Palanisamy

et al. 2021

Anal. Chem.

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Pyrylium salts are considered efficient chemical tags for amino groups. However, the apparent steric selectivity of pyrylium salts limits their application in the field of chemical labeling, especially during the labeling of sterically hindered compounds like amino acids, peptides, and proteins. Herein, we have investigated the effects of the α-substitution of pyrylium salts on their reactivity. We have also investigated the mechanism of nucleophilic reactions with pyrylium salts and further proposed that the reactivity of pyrylium salts mainly depends on the position and type of their substituents. A series of pyrylium salts were synthesized, and a highly active α-monosubstituted pyrylium salt, 2,4,5-triphenylpyrylium, was developed for efficient chemical labeling. All of the 15 amino acids studied were efficiently labeled under optimized reaction conditions. The 2,4,5-triphenylpyrylium salt was highly efficient in comparison to the previously reported 2,4,6-triphenylpyrylium salt developed for lysine-specific modifications. Furthermore, we successfully used 2,4,5-triphenylpyrylium salt for the hydrophobic labeling of peptides and protein hydrolysates. The most striking observation was that the ionization efficiency of short-chain multilabeled peptides in mixed samples, after derivatization, increased by up to 60 times. The increase in ionization efficiency gradually decreased with increasing peptide chain length. During the “soft” collision-induced dissociation (CID) process, the peptide was tagged at the N-terminus with 2,4,5-triphenylpyrylium, producing abundant a-type ions and b-type ions (Δ = 28), which eases the peptide resequencing process and assists in cracking the peptide codes. Moreover, 2,4,5-triphenylpyrylium has been utilized for the proteomic analysis of HeLa cell digests. In addition, 215 additional proteins were identified in the labeled products and the coverage of most proteins was improved.

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Section: Resultsmentioning

confidence: 99%

α-Active Pyrylium Salt 2,4,5-Triphenylpyrylium for Improved Mass Spectrometry-Based Detection of Peptides

Huang

Palanisamy

et al. 2021

Anal. Chem.

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“…[33,36] A mixture of the cyclopentadiene derivatives (0.62 mmol) and perchloric acid (70 %, 1 mL) in toluene/acetonitrile (3:1, 15 mL) was stirred at room temperature for 3 d. Diethyl ether (30 mL) was poured into the mixture. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.…”

Section: Methodsmentioning

confidence: 99%

“…[27][28][29][30] In contrast, ring-opening reactions of pyrylium salts have been rarely studied. In our continuing research on the synthesis, optical properties, and reactivity of pyrylium salts, [33][34][35][36] we became interested in constructing decatetraene diketone derivatives by dimerization of pyrylium salts. In our continuing research on the synthesis, optical properties, and reactivity of pyrylium salts, [33][34][35][36] we became interested in constructing decatetraene diketone derivatives by dimerization of pyrylium salts.…”

Section: Introductionmentioning

confidence: 99%

One‐Step Stereoselective Synthesis of (2Z,4Z,6Z,8Z)‐Decatetraene Diketone from Pyrylium Salts

Yang

Gao

et al. 2013

Eur J Org Chem

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A strategy for the stereoselective synthesis of (2Z,4Z,6Z,8Z)‐decatetraene diketone by the one‐step metal reduction of pyrylium salts is described. Reduction of α‐active pyrylium salts (at least one H at the α‐C positon) leads to only linear decatetraene diketone derivatives, whereas reduction of α‐non‐active pyrylium salts (no H at the α‐C position) generates two unexpected structures and one linear decatetraene diketone. The reaction conditions were optimized, and a reaction mechanism was proposed. Single‐crystal structures of decatetraene diketone derivatives demonstrate the twisted configuration of the backbones and the all‐(Z) geometry of the double bonds. In addition, the thermal, optical, and electrochemical properties of these compounds were studied in detail.

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“…Pyrylium salts, were prepared according to our previously reported work. 10 The key characteristic of pyrylium salts is the amonosubstitution named a-active pyrylium salts, we designed and synthesized several functional organic molecules in our previous work. 11 In order to access PBI frameworks, we rst converted the active pyrylium salts into corresponding pyridinium salts with one active amino group neighboring the "aactive" C-H bonds (Scheme 2).…”

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confidence: 99%

Construction of fluorescence-tunable pyrido-fused benzimidazoles via direct intramolecular C–H amination under transition-metal-free conditions

Gong

Gao

et al. 2014

RSC Adv.

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A Facile Oxidation and Oxygen Insertion of the Cyclopentadiene Ring by Molecular Oxygen in Solution

Cited by 19 publications

References 42 publications

α-Active Pyrylium Salt 2,4,5-Triphenylpyrylium for Improved Mass Spectrometry-Based Detection of Peptides

α-Active Pyrylium Salt 2,4,5-Triphenylpyrylium for Improved Mass Spectrometry-Based Detection of Peptides

One‐Step Stereoselective Synthesis of (2Z,4Z,6Z,8Z)‐Decatetraene Diketone from Pyrylium Salts

Construction of fluorescence-tunable pyrido-fused benzimidazoles via direct intramolecular C–H amination under transition-metal-free conditions

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