Interpretation of enantioresolution in nordeoxycholic acid channels based on the four-location model

Chirality

Volumn 15, Issue 1, 2003, Pages 53-59

  Kato, Kazuaki ^a   Aoki, Yuriko ^a   Sugahara, Michihiro ^a   Tohnai, Norimitsu ^a   Sada, Kazuki ^a   Miyata, Mikiji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Chiral recognition; Difference Fourier map; Inclusion compounds; Packing manner; Three point attachment model

Indexed keywords

ALKANOL; DEOXYCHOLIC ACID DERIVATIVE; PENTANOL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

DEOXYCHOLIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0037214297     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10159     Document Type: Article

References (22)

1. Toda F, Tanaka K, Ueda H. A new optical resolution method of tertiary acetylenic alcohol utilizing complexation with brucine. Tetrahedron Lett 1981;22:4669-4673.
2. Arad-Yellin R, Green BS, Knossow M, Tsoucaris G. Chiral discrimination in crystalline tri-o-thymotide clathrate inclusion complexes. Chemical and crystallographic studies. J Am Chem Soc 1983;105:4561-4571.
3. Worcsh D, Vögtle F, Kirfel A, Will G. Salze optisch aktiver alkaloide als enantiodifferenzierende einschlusbildner. Naturwissenschaften 1984; 71:423-424.
4. Weber E, Wimmer C, Llamas-Saiz AL, Forces-Foces C. New chiral selectors derived from lactic acid. Cocrystalline and sorptive optical resolutions, and the crystal structure of an inclusion complex with 3-methylcyclohexanone. J Chem Soc Chem Commun 1992;733-735.
5. Tanaka K, Okada T, Toda F. Separation of the enantiomers of 2,2′-dihydroxy-1,1′-binaphthyl and 10,10′-dihydroxy-9,9′-biphenanthryl by complexation with N-alkylcinchonidinium halides. Angew Chem Int Ed Engl 1993;32:1147-1148.
6. Sada K, Kondo T, Miyata M. Resolution of aliphatic alcohols by hydrogen bond "double hooks" of cholanamide inclusion compounds. Tetrahedron Asymm 1995;6:2655-2656.
7. Kozma D, Böcskei Z, Kassai C, Simon K, Fogassy E. Optical resolution of racemic alcohols by diastereoisomeric complex formation with O,O′-dibenzoyl-(2R, 3R)-tartaric acid; the crystal structure of the (-)-(1R, 2S,5R) -menthol. O,O′-dibenzoyl-(2R,3R)-tartaric acid complex. Chem Commun 1996;753-754.
8. Raymond G. Tri-o-thymotide and related hosts. In: MacNicol DD, Toda F, Bishop R, editors. Comprehensive Supramolecular Chemistry. Oxford: Pergamon; 1996:6. p 239-280.
9. Akazome M, Noguch M, Tanaka O, Sumikawa A, Uchida T, Ogura K. Enantiomeric recognition of alkyl phenyl sulfoxides by crystalline (R)-phenylglycyl-(R)-phenylglycine. Tetrahedron 1997;53:8315-8322.
10. Tanaka K, Toda F, Preparation of optically pure 2,3-epoxycyclohexanones. J Chem Soc Chem Commun 1983;1513-1514.
11. Toda F, Tanaka K, Kido M. An efficient optical resolution of 2-methylpiperazine was achieved by complex formation with optically active 1-phenyl-1-(o-chlorophenyl)prop-2-yn-1-o1 and 1,6-diphenyl-1,6-di(ochlorophenyl)hexa-2,4-diyne-1,6-diol. Chem Lett 1988;513-516.
12. Toda F. Isolation and optical resolution of materials utilizing inclusion crystallization. In: Weber E, editor. Topics in Current Chemistry. Berlin: Springer; 1987;140, p 44-69,
13. Toda F. In: Gokel GW, editor. Molecular Recognition in the Solid State. Advances in Supramolecular Chemistry. Hampton Hill, UK: JAI Press; 1992. p 141-191.
14. Miyata M, Sada K. Deoxycholic acid and related hosts. In: MacNicol DD, Toda F, Bishop R, editors. Comprehensive Supramolecular Chemistry. Oxford: Pergamon; 1996:6. p 147-176.
15. Miyata M, Sada K, Miyake Y. Chiral recognition of organic substances by using bile acids/salts and their derivatives, In: Hinze WL, editor. Bile Acid/Salt Surfactant Systems. Stamford, CT: JAI Press; 2000. p 205-228.
16. Aoki Y, Hishikawa Y, Sada K, Miyata M. Enantioresolution of aliphatic alcohols by lithocholamide. Enantiomer 2000;5:95-104.
17. Sada K, Nakano K, Hirayama K, Miyata M, Sasaki S, Takemoto K, Kasai N, Kato K, Shigesato M, Miki K. Molecular recognition of medium-size lactones by enclathration of cholic acid. Supramol Chem 2001;13:35-44.
18. Ogston AG. Interpretation of experiments on metabolic processes, using isotopic tracer elements, Nature 1948;163:963.
19. Easson LH, Stedman E. CLXX studies on the relationship between chemical constitution and physiological action. Biochem J 1933;27: 1257-1266.
20. Mesecar AD, Koshland DE Jr. A new model for protein stereospecificity. Nature 2000;403:614-615.
21. Schteingart CD, Hofmann AF. Synthesis of 24-nor-5b-cholan-23-oic acid derivatives: A convenient and efficient one-carbon degradation of the side chain of natural bile aciss. J Lipid Res 1988;29:1387-1395.
22. Taber DF, Wang Y. Synthesis of (-)-haliclonadiamine. J Am Chem Soc 1997;119:22-26.