1. On-Demand Chirality Transfer of Human Serum Albumin to Bis(thiophen-2-yl)hexafluorocyclopentenes through Their Photochromic Ring Closure
- Author
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Takashi Ubukata, Yasushi Yokoyama, Aki Nitta, Tetsuya Nakagawa, Izuru Kawamura, Megumi Kayanuma, Yuri Saeki, and Yasuteru Shigeta
- Subjects
chemistry.chemical_classification ,Molecular Structure ,Organic Chemistry ,Enantioselective synthesis ,Serum Albumin, Human ,Thiophenes ,Ring (chemistry) ,Human serum albumin ,Medicinal chemistry ,chemistry.chemical_compound ,Photochromism ,Dicarboxylic acid ,chemistry ,Diarylethene ,medicine ,Humans ,Molecule ,Chirality (chemistry) ,medicine.drug - Abstract
Photochromic 1,2-bis(5-carboxy-3-methyl-2-thienyl)hexafluorocyclopentene and its dimethyl ester incorporated in human serum albumin (HSA) showed highly enantioselective photochromic ring-closing reactions upon 366 nm light irradiation. The absolute stereochemistry of the major ring-closed form of the dicarboxylic acid at the newly formed sp3 carbon atoms was determined to be (S,S) by the process of docking simulation of the diarylethene molecule and HSA followed by molecular dynamics calculations and comparison of the measured and calculated CD spectra. Esterification of the major closed form of the diacid gave the minor closed form of the diester. The absolute stereochemistry of the major diester was thus determined to be (R,R).
- Published
- 2021
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