Supramolecular tilt chirality in crystals of steroids and alkaloids

Chirality

Volumn 20, Issue 3-4, 2008, Pages 330-336

  Hisaki, Ichiro ^a   Tohnai, Norimitsu ^a   Miyata, Mikiji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Brucine; Cholic acid; Cinchona alkaloid; Crystallography; Helical structure; Molecular assembly; Twofold screw axis

Indexed keywords

ALKALOID; BILE ACID; BRUCINE; CINCHONA ALKALOID; STEROID;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MATHEMATICAL ANALYSIS; PRIORITY JOURNAL; REVIEW; SUPRAMOLECULAR CHEMISTRY;

ALKALOIDS; BILE ACIDS AND SALTS; CINCHONA ALKALOIDS; CRYSTALLIZATION; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; STEREOISOMERISM; STEROIDS; STRYCHNINE;

EID: 39749107313     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20443     Document Type: Review

References (31)

1. Atwood JL, Steed JW, editors. Encyclopedia of supramolecular chemistry. New York: Marcel Decker; 2004.
2. Cahn RS, Ingold CK, Prelog V. Specification of asymmetric configuration in organic chemistry. Experientia 1956;12:81-124.
3. Cahn RS, Ingold CK, Prelog V. Specification of molecular chirality. Angew Chem Chem Int Ed Engl 1966;5:385-415.
4. Noyori R, Asymmetric catalysis in organic synthesis. New York: Wiley; 1994.
5. Crego-Calama M, Reinhoudt DN, editors. Supramolecular chirality. Berlin: Springer; 2006.
6. Gardner M. The new ambidextrous universe. New York: W. H. Freeman; 1990.
7. Anet FAL, Miura SS, Siegel J, Mislow K. La Coupe Du Roi and its relevance to stereochemistry. Combination of two homochiral molecules to give an achiral product. J Am Chem Soc 1983;105:1419-1426.
8. Tashiro K, Konishi K, Aida T. Enantiomeric resolution of chiral metallobis(porphyrin)s: studies on rotatability of electronically coupled porphyrin ligands. Angew Chem Int Ed Engl 1997;36:856-858.
9. Takeuchi M, Imada T, Shinkai S. A strong positive allosteric effect in the molecular recognition of dicarboxylic acids by a cerium(iv) bis[tetrakis(4-pyridyl)-porphyrinate] double decker. Angew Chem Int Ed 1998;37:2096-2099.
10. Mori T, Sekine T, Watanabe J, Furukawa T, Takezoe H. Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules. J Mater Chem 1996;6:1231-1233.
11. Link DR, Natale G, Shao R, Maclennan EJ, Clark NA, Körblova E, Walba DM. Science 1997;278:1924-1927.
12. Nakano K, Sada K, Miyata M. Inclusion compounds of cholic acid with various hydrocarbons and the crystal structure of a 1:1 complex of cholic acid and benzene. Chem Lett 1994;137-140.
13. 1 helical assembly. Chem Asian J 2007;2:230-238.
14. Kitaigorodskii AI. Molecular crystals and molecules. London: Academic Press; 1973.
15. Yao JW, Cole JC, Pidcock E, Allen FH, Howard JAK, Motherwell WDS. CSD symmetry: the definitive database of point-group and space-group symmetry relationships in small-molecule crystal structures. Acta Crystallogr Sect B 2002;58:640-646.
16. Pérez-García L, Amabilino DB. Spontaneous resolution under supramolecular control. Chem Soc Rev 2002:31;342-356.
17. Matsuura T, Koshima H. Introduction to chiral crystallization of achiral organic compounds: Spontaneous generation of chirality. J Photochem Photobiol C Photochem Rev 2005;6:7-24.
18. Norsten TB, McDonald R, Branda NR. The self-assembly and spontaneous resolution of a hydrogen-bonded helix. Chem Commun 1999;719-720.
19. Jayanty S, Radhakrishnan TP. Spontaneous resolution through helical assembly of a conformationally chiral molecule with an unusual zwitterionic structure. Chem Eur J 2004;10:2661-2667.
20. Yi L, Yang X, Lu T, Cheng P. Self-assembly of right-handed helical infinite chain, one- and two-dimensional coordination polymers tuned via anions. Cryst Growth Design 2005;5:1215-1219.
21. Miyata M, Sada K. Deoxycholic acid and related hosts. In: MacNicol DD, Toda F, Bishop R, editors. Solid-state supramolecular chemistry, comprehensive supramolecular chemistry, Vol. 6. Pergamon: Oxford; 1996. pp 147-176.
22. Watabe T, Kobayashi K, Kato K, Sada K, Miyata M. Hierarchical structure of brucine inclusion crystals with neutral guest molecules: chiral tapes and their bundles. Mol Cryst Liq Cryst 2005;440:117-124.
23. Kato K, Tohnai N, Miyata M. Hierarchical prediction process of cholic acid crystal structures based on characteristic helical assemblies. Mol Cryst Liq Cryst 2005;440:125-132.
24. 1 helical columnar assembly. Chem Lett 2006;35:806-807.
25. Watabe T, Kobayashi K, Hisaki I, Tohnai N, Miyata M. Guest-induced supramolecular isomerism and chirality of brucine inclusion crystals with aliphatic alcohols: a hierarchical interpretation. Bull Chem Soc Jpn 2007;80:464-475.
26. 1 helical assemblies with the molecular tilt as well as three-directional and facial chirality. Chem Lett 2007;36:234-235.
27. Gould RO, Walkinshaw MD. Molecular recognition in model crystal complexes: the resolution of D and L amino acids. J Am Chem Soc 1984;106:7840-7842.
28. Dijksma FJJ, Gould RO, Parsons S, Taylor P, Walkinshaw MD. Promiscuous recognition of the hexapyranose epimers α,β-D-glucuronic and α,β-D-galacturonic acids between corrugated brucine sheets. Chem Commun 1998;745-746.
29. Kato K, Inoue K, Tohnai N, Miyata M. Helical tape assemblies in inclusion crystals of bile acids and their derivatives. J Inclusion Phenom Macrocyclic Chem 2004;48:61-67.
30. Dehmlow EV, Düttmann S, Neumann B, Stammler HG. Monodeazacinchona alkaloid derivatives: synthesis and preliminary applications as phase-transfer catalysts. Eur J Org Chem 2002;2087-2093.
31. 1 helical assemblies of cinchona alkaloids in crystals: definition of their handedness based on the molecular tilt. Chem Lett 2006;35:1274-1275.