Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties

Miyata, Kota; Yasuda, Satoru; Masuya, Takuto; Ito, Satoshi; Kinoshita, Yusuke; Tamiaki, Hitoshi; Oba, Toru

doi:10.1016/j.tet.2018.05.040

Cited by 4 publications

(1 citation statement)

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“…A new method for the conversion of the vinyl groups of 3 to formyl and acetyl moieties, respectively, while circumventing the use of OsO 4 was introduced by Oba and co‐workers . The reaction of the vinyl groups with iodine and PIFA in ethylene glycol/1,2‐dichloroethane gave a diiodoether porphyrin which was converted to 3,8‐diacetyl porphyrin.…”

Section: Synthesis Of Ppix Derivativesmentioning

confidence: 99%

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

Sitte

Senge

2020

Eur J Org Chem

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Protoporphyrin IX (PPIX) is the porphyrin scaffold of heme b, a ubiquitous prosthetic group of proteins responsible for oxygen binding (hemoglobin, myoglobin), electron transfer (cytochrome c) and catalysis (cytochrome P450, catalases, peroxidases). PPIX and its metallated derivatives frequently find application as therapeutic agents, imaging tools, catalysts, sensors and in light harvesting. The vast toolkit of accessible porphyrin functionalization reactions enables easy synthetic modification of PPIX to meet the requirements for its multiple uses. In the past few years, particular interest has arisen in exploiting the interaction of PPIX and its synthetic derivatives with biomolecules such as DNA and heme‐binding proteins to evolve molecular devices with new functions as well as to uncover potential therapeutic toeholds. This review strives to shine a light on the most recent developments in the synthetic chemistry of PPIX and its uses in selected fields of chemical biology.

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Section: Synthesis Of Ppix Derivativesmentioning

confidence: 99%

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

Sitte

Senge

2020

Eur J Org Chem

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New amide derivatives of blood porphyrins bearing ethanolamine moieties

Rocheva

Белых

2023

Russ Chem Bull

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C3¹-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

et al. 2019

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Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties

Cited by 4 publications

References 44 publications

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

New amide derivatives of blood porphyrins bearing ethanolamine moieties

C3¹-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

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Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties

Cited by 4 publications

References 44 publications

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

New amide derivatives of blood porphyrins bearing ethanolamine moieties

C31-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative

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Product

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C3¹-Selective substitution of cationic N-heteroaromatic groups into a 3-vinylated chlorophyll-a derivative