Synthesis of chlorophyll- a derivatives methylated in the 3-vinyl group and their intrinsic site energy
| Autor: | Tomohiro Miyatake, Yuki Kimura, Kazuki Tsuji, Masaki Kuno, Hiroaki Watanabe, Hitoshi Tamiaki |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Chlorophyll
Chlorophyll a Porphyrins Stereochemistry Clinical Biochemistry Molecular Conformation Pharmaceutical Science 010402 general chemistry Methylation 01 natural sciences Biochemistry Medicinal chemistry chemistry.chemical_compound Group (periodic table) Drug Discovery Absorption (electromagnetic radiation) Molecular Biology Conformational isomerism 010405 organic chemistry Organic Chemistry 0104 chemical sciences Models Chemical chemistry Chlorin Wittig reaction Molecular Medicine |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 26:3034-3037 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2016.05.008 |
| Popis: | Wittig reaction of methyl pyropheophorbide-d possessing the 3-formyl group gave readily methyl pyropheophorbides-a bearing a variety of 3-alkenyl groups as semi-synthetic models of chlorophyll-a. The 3-substituents rotated around the C3-C3(1) bond from the coplanar conformation with the chlorin π-system, moving the redmost visible absorption maxima to a shorter wavelength. The model experiments showed that natural chlorophyll-a carrying the 3-vinyl group would take a similar rotamer to control its intrinsic site energy. |
| Databáze: | OpenAIRE |
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