Stereoisograms for reorganizing the theoretical foundations of stereochemistry and stereoisomerism. Part 3: rational avoidance of misleading standpoints for pro-R/pro-S-descriptors |
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| Affiliation: | 1. GE Healthcare, The Grove Centre, White Lion Road, Amersham, Buckinghamshire, HP7 9LL, UK;2. GE Healthcare AS, Nycoveien 1-2 Postboks 4220 Nydalen, Oslo, 0401, NO;1. Department of Health Services Management and Policy, Kyushu University Graduate School of Medicine, Higashi-ku, Fukuoka 812-8582, Japan;2. Department of Emergency and Critical Care Center, Kyushu University Hospital, Higashi-ku, Fukuoka 812-8582, Japan;3. Welfare Department, the City of Shimonoseki, 1-1 Nanbu-cho, Shimonoseki, Yamaguchi 750-8521, Japan |
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| Abstract: | The stereoisogram approach is introduced to settle the misleading terminology due to ‘prochirality’ in modern stereochemistry. After the term prochirality is redefined as having a purely geometric meaning, a method based on probe stereoisograms and another method based on equivalence classes (orbits) are introduced to determine prochirality and/or pro-RS-stereogenicity. Enantiotopic and RS-diastereotopic relationships appearing in probe stereoisograms are respectively used to determine prochirality and pro-RS-stereogenicity, where ‘stereoheterotopic’ relationships used in modern stereochemistry are abandoned. Alternatively, an enantiospheric orbit for specifying prochirality and an RS-enantiotropic orbit for specifying pro-RS-stereogenicity are emphasized by using coset representations and Young tableaux. The pro-R/pro-S-system is clarified to be based on pro-RS-stereogenicity and not on prochirality. |
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