Synthesis of chlorophyll-a homologs by C132-substitutions and their physico- and biochemical properties
| Autor: | Yuki Egami, Shin Ogasawara, Mitsuaki Hirose, Hitoshi Tamiaki |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Circular dichroism
Chlorophyllase 010405 organic chemistry Stereochemistry Organic Chemistry macromolecular substances 01 natural sciences Biochemistry Fluorescence 0104 chemical sciences 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Hydrolysis chemistry Chlorophyll Drug Discovery polycyclic compounds Michael reaction Nucleophilic substitution Methyl acrylate Molecular Biology |
| Zdroj: | Bioorganic Chemistry. 94:103383 |
| ISSN: | 0045-2068 |
| DOI: | 10.1016/j.bioorg.2019.103383 |
| Popis: | A mixture of pheophytins-a/a', metal-free forms of photosynthetically active chlorophyll(Chl)s-a/a' bearing the 132-methoxycarbonyl group, was substituted at the C132-position by bimolecular nucleophilic substitution with methyl bromoacetate or Michael addition with methyl acrylate, followed by C132-demethoxycarbonylation and magnesium insertion at the central position, to afford Chl-a/a' homologs possessing a methoxycarbonylmethyl or 2-methoxycarbonylethyl group at the C132-position, respectively. These C132-methylene- and ethylene-inserted homologs were characterized by 1D/2D 1H NMR spectroscopy, and the optical properties of their C132-epimerically pure samples are investigated using visible absorption, fluorescence emission, and circular dichroism spectroscopies. The stereochemistry at the C132-chiral center of these Chl-a/a' homologs was not inverted in a basic solution, and the Chl-a homologs were effective for the substrates for the chlorophyllase reaction, hydrolysis of the phytyl ester. |
| Databáze: | OpenAIRE |
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