Manual construction and mathematics- and computer-aided counting of stereoisomers. The example of oligoinositols

Journal of Chemical Information and Computer Sciences

Volumn 44, Issue 5, 2004, Pages 1654-1665

  Rücker, Christoph ^a   Gugisch, Ralf ^a   Kerber, Adalbert ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPUTER APPLICATIONS; ERROR ANALYSIS; STEREOCHEMISTRY; TOPOLOGY;

COMPUTER-AIDED COUNTING; OLIGOINOSITOLS; STEREOCENTERS; STEREOISOMERS;

OLIGOMERS;

EID: 5444242143     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci040102z     Document Type: Article

References (21)

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3. Dolhaine, H.; Honig, H. Full Isomer-Tables of Inositol-Oligomers up to Tetramers. MATCH Commun. Math. Comput. Chem. 2002, 46, 91-119.
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8. Eliel, E. L. Stereochemistry of Organic Compounds; Wiley: New York, 1994.
9. Signs (+) and (-) in the names of the chiro-inositols refer to the sense of optical rotation. In the present work, however, we use these descriptors to identify the absolute configuration of a chiro-inositol derivative: The (+) sign denotes the absolute configuration of (+)-chiro-inositol.
10. 2). Any manipulation at one or the other of two such substituents results in two distinct products, two enantiomers in the simplest case. Two features in a molecule are diastereotopic if they are not related by any symmetry. Any manipulation at one or the other results in two diastereomers. For more information see ref 5 or the following: Rücker, C.; Braun, J. UNIMOLIS - A Computer-aided Course on Molecular Symmetry and Isomerism, http://unimolis.uni-bayreuth.de (C.A. 140:235199 2004).
11. Two like substituents here are either identical or enantiomeric, unlike substituents are diastereomeric or not stereoisomeric.
12. Since the enantiomorphs of letters F, G, and R are not available in common word processors nor in common molecule drawing programs, we here use instead the letters preceded by a minus sign.
13. As seen in Figures 7 and 8 and in Table 2, a class 2 entry results in exactly twice as many isomers as a class 1 entry. This factor of 2 is fully explained by the difference in chirality: A pair of enantiomers (class 2) results in two products where a single species (class 1) gives one product. In other words, there is no difference in the number of products obtained from two enantiotopic or from two diastereotopic OX groups. This is also seen in Figures 4 and 5 and Table 1 (and Figures 10 and 11 and Table 3). This is an immediate consequence of the definitions of enantiotopic and diastereotopic molecular features, see Note 7. If we are interested in the number of products only, we are therefore allowed to combine cases of enantiotopic and of diastereotopic OX groups in a single class, as it was done in class 1 for 5. In fact the classifications of disubstituted inositols made above are somewhat arbitrary, except for the distinction between homotopic OX groups on one hand and enantiotopic/diastereotopic OX groups on the other, which is compulsory.
14. Kerber, A. Applied Finite Group Actions, 2nd ed.; Springer: Berlin, 1999; Chapter 2.
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17. 2×G.
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20. (a) Wieland, T. Erzeugung, Abzählung und Konstruktion von Stereo-isomeren. MATCH Commun. Math. Comput. Chem. 1994, 31, 153-203.
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