Atropdiastereoisomers of ellagitannin model compounds: Configuration, conformation, and relative stability of D-glucose diphenoyl derivatives

Tetrahedron Asymmetry

Volumn 11, Issue 12, 2000, Pages 2495-2507

  Immel, Stefan ^a   Khanbabaee, Karamali ^b  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b Fb Chem Chemietechnik Univ G   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

D GLUCOSE DIPHENOYL DERIVATIVE; ELLAGITANNIN; GLUCOPYRANOSIDE; GLUCOSE; GLUCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIASTEREOISOMER; DRUG CONFORMATION; DRUG STABILITY; DRUG STRUCTURE; ENERGY; ESTERIFICATION; MOLECULAR DYNAMICS; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0034733521     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00179-8     Document Type: Article

References (36)

1. Part 28 of the series Molecular Modelling of Saccharides. For Part 27 see: Immel, S.; Nakagawa, T.; Lindner, H.-J.; Lichtenthaler, F. W. Chem. Eur. J. 2000, 6, in press.
2. For a review, see: Quideau, S.; Feldmann, K. S. Chem. Rev. 1996, 96, 475-503.
3. Nonaka, G.-I.; Ishimatsu, M.; Ageta, M.; Nishioka, I. Chem. Pharm. Bull. 1989, 37, 50-53.
4. Tanaka, T.; Kirahara, S.; Nonaka, G.-I.; Nishioka, I. Chem. Pharm. Bull. 1993, 41, 1708-1716.
5. Feldmann, K. S.; Smith, R. S. J. Org. Chem. 1996, 61, 2606-2612.
6. Khanbabaee, K.; Lötzerich, K. J. Org. Chem. 1998, 63, 8723-8728.
7. Khanbabaee, K.; Lötzerich, K. Liebigs Ann./Recueil 1997, 1571-1575.
8. Khanbabaee, K.; Lötzerich, K.; Borges, M.; Großer, M. J. Prakt. Chem. 1999, 341, 159-166.
9. Khanbabaee, K.; Schulz, C.; Lötzerich, K. Tetrahedron Lett. 1997, 38, 1367-1368.
10. Khanbabaee, K.; Lötzerich, K. Eur. J. Org. Chem. 1999, 3079-3083.
11. (a) Schmidt, O. T.; Schmidt, D. M.; Herok, J. Liebigs Ann. Chem. 1954, 587, 67-74.
12. (b) Schmidt, O. T.; Blinn, F.; Lademann, R. Liebigs Ann. Chem. 1952, 576, 75-84.
13. (c) Schmidt, O. T.; Schmidt, D. M. Liebigs Ann. Chem. 1952, 578, 31-33.
14. Haddock, E. A.; Gupta, R. K.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1982, 2535-2345.
15. Okuda, T.; Yoshida, T.; Hatano, T. J. Chem. Soc., Perkin Trans. 1 1982, 9-14.
16. Tanaka, T.; Nonaka, G.-I.; Nishioka, I.; Miyahara, K.; Kawasaki, T. J. Chem. Soc., Perkin Trans. 1 1986, 369-376.
17. Gupta, R. K.; Al-Shafi, S. M. K.; Layden, K.; Haslam, E. J. Chem. Soc., Perkin Trans. 1 1982, 2525-2534.
18. Haslam, E. Prog. Chem. Org. Nat. Prod. 1982, 41, 1-46.
19. 2 To the best of our knowledge, no models for the formation of 3,6-O- or 2,4-O-HHDP ellagitannins have been put forth on an atomic level. The Monte-Carlo (MC) simulations described in Ref. 2 did also not allow to carry out a comprehensive geometry analysis of the complex fused ring systems of the ellagitannins.
20. 20.
21. Luger, P.; Weber, M.; Kashino, S.; Amakura, Y.; Yoshida, T.; Okuda, T.; Beurskens, G.; Dauter, Z. Acta Crystallogr., Sect. B 1998, 54, 687-694.
22. Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700-3705; erroneously the mirror image geometry of 13 is filed in the CCDF.
23. (a) Cremer, D. A.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354-1358.
24. (b) Jeffrey, G. A.; Taylor, R. Carbohydr. Res. 1980, 81, 182-183.
25. 23 For the C-4 epimer galactose, the conformers are populated in the order gt≈tg>gg (Scheme 1).
26. (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin/New York, 1991.
27. (b) Kroon-Batenburg, L. M. J.; Kroon, J. Biopolymers 1990, 29, 1243-1248.
28. (c) Bock, K.; Duus, J. Ø. J. Carbohydr. Chem. 1994, 13, 513-543.
29. Yang, D.; Yip, Y.-C.; Tang, M.-W.; Wong, M.-K.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1996, 118, 491-492.
30. To the best of our knowledge, D-galactose or D-mannose derived ellagitannins are not known to occur in nature; but we envisage their chemical synthesis as an interesting target.
31. 4 anti-chair geometries of their pyranose portions.
32. 2O-) the (R)-atropisomers are preferred over the (S)-forms.
33. Tanaka, T.; Tong, H.-H.; Xu, Y.- M.; Ishimaru, K.; Nonaka, G.-I.; Nishioka, I. Chem. Pharm. Bull. 1992, 40, 2975-2980.
34. +: Molecular Architecture Modeling Program; Darmstadt University of Technology, 2000.
35. Lindner, H. J.; Kroeker, M. PIMM91-Closed Shell PI-SCF-LCAO-MO-Molecular Mechanics Program; Darmstadt University of Technology, 1997. Smith, A. E.; Lindner, H. J. J. Comput.-Aided Mol. Des. 1991, 5, 235-262.
36. Lindner, H. J.; Kroeker, M. PIMM91-Closed Shell PI-SCF-LCAO-MO-Molecular Mechanics Program; Darmstadt University of Technology, 1997. Smith, A. E.; Lindner, H. J. J. Comput.-Aided Mol. Des. 1991, 5, 235-262.