High guest inclusion in 3β-amino-7α,12α-dihydroxycholan-24-oic acid enabled by charge-assisted hydrogen bonds

Tetrahedron

Volumn 62, Issue 29, 2006, Pages 6808-6813

  Ryu, Eui Hyun ^a   Ellern, Arkady ^a   Zhao, Yan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Bile acids; Crystal engineering; Crystal structures; Hydrogen bonds; Inclusion compounds

Indexed keywords

3BETA AMINO 7ALPHA,12ALPHA DIHYDROXYCHOLAN 24 OIC ACID; AMMONIA; CARBOXYLIC ACID; CHOLIC ACID DERIVATIVE; METHANOL; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLOGRAPHY; HYDROGEN BOND; HYDROPHOBICITY; PRIORITY JOURNAL;

EID: 33744942925     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.04.094     Document Type: Article

References (65)

1. For some examples of supramolecular systems constructed from cholic acid, see:
2. Davis A.P., Bonar-Law R.P., and Sanders J.K.M. In: Atwood J.L., Davis J.E.D., MacNicol D.D., and Vögtle F. (Eds). Comprehensive Supramolecular Chemistry Vol. 4 (1996), Pergamon, New York, NY Chapter 7, and references therein
3. Li Y., and Dias J.R. Chem. Rev. 97 (1997) 283-304 and references therein
4. Maitra U. Curr. Sci. 71 (1996) 617-624
5. Smith B.D., and Lambert T.N. Chem. Commun. (2003) 2261-2268 and references therein
6. Davis A.P., and Joos J.-B. Coord. Chem. Rev. 240 (2003) 143-156 and references therein
7. Burrows C.J., and Sauter R.A. J. Inclusion. Phenom. 5 (1987) 117-121
8. Janout V., Lanier M., and Regen S.L. J. Am. Chem. Soc. 118 (1996) 1573-1574
9. Ariga K., Terasaka Y., Sakai D., Tsuji H., and Kikuchi J.-I. J. Am. Chem. Soc. 122 (2000) 7835-7836
10. Werner F., and Schneider H.-J. J. Inclusion Phenom. Macro. Chem. 41 (2001) 37-40
11. Yoshino N., Satake A., and Kobuke Y. Angew. Chem. Int. Ed. 40 (2001) 457-459
12. Zhao Y., and Zhong Z. J. Am. Chem. Soc. 127 (2005) 17894-17901
13. Janout V., Lanier M., and Regen S.L. J. Am. Chem. Soc. 118 (1996) 1573-1574
14. Janout V., Lanier M., and Regen S.L. J. Am. Chem. Soc. 119 (1997) 640-647
15. Janout V., Di Giorgio C., and Regen S.L. J. Am. Chem. Soc. 122 (2000) 2671-2672
16. Janout V., Zhang L.-h., Staina I.V., Di Giorgio C., and Regen S.L. J. Am. Chem. Soc. 123 (2001) 5401-5406
17. Janout V., Jing B., Staina I.V., and Regen S.L. J. Am. Chem. Soc. 125 (2003) 4436-4437
18. Jing B., Janout V., Herold B.C., Klotman M.E., Heald T., and Regen S.L. J. Am. Chem. Soc. 126 (2004) 15930-15931
19. Ariga K., Terasaka Y., Sakai D., Tsuji H., and Kikuchi J.-I. J. Am. Chem. Soc. 122 (2000) 7835-7836
20. Ariga K., Nakanishi T., Terasaka Y., Tsuji H., Sakai D., and Kikuchi J.-I. Langmuir 21 (2005) 976-981
21. Ghosh S., and Maitra U. Org. Lett. 8 (2006) 399-402
22. For other examples of facial amphiphiles, see:
23. Stein T.M., and Gellman S.H. J. Am. Chem. Soc. 114 (1992) 3943-3950
24. Cheng Y., Ho D.M., Gottlieb C.R., Kahne D., and Bruck M.A. J. Am. Chem. Soc. 114 (1992) 7319-7320
25. Venkatesan P., Cheng Y., and Kahne D. J. Am. Chem. Soc. 116 (1994) 6955-6956
26. McQuade D.T., Barrett D.G., Desper J.M., Hayashi R.K., and Gellman S.H. J. Am. Chem. Soc. 117 (1995) 4862-4869
27. Broderick S., Davis A.P., and Williams R.P. Tetrahedron Lett. 39 (1998) 6083-6086
28. Isaacs L., Witt D., and Fettinger J.C. Chem. Commun. (1999) 2549-2550
29. Taotafa U., McMullin D.B., Lee S.C., Hansen L.D., and Savage P.B. Org. Lett. 2 (2000) 4117-4120
30. Arnt L., and Tew G.N. J. Am. Chem. Soc. 124 (2002) 7664-7665
31. Willemen H.M., Marcelis A.T.M., and Sudhölter E.J.R. Langmuir 19 (2003) 2588-2591
32. Elemans J.A.A.W., Slangen R.R.J., Rowan A.E., and Nolte R.J.M. J. Org. Chem. 68 (2003) 9040-9049
33. Zhong Z., Yan J., and Zhao Y. Langmuir 21 (2005) 6235-6239
34. Menger F.M., and Sorrells J.L. J. Am. Chem. Soc. 128 (2006) 4960-4961
35. Ryu E.-H., and Zhao Y. Org. Lett. 6 (2004) 3187-3189
36. Zhao Y., and Ryu E.-H. J. Org. Chem. 70 (2005) 7585-7591
37. Zhao Y., and Zhong Z. J. Am. Chem. Soc. 127 (2005) 17894-17901
38. For two reviews, see:
39. Miyata M., and Sada K. In: Atwood J.L., Davis J.E.D., MacNicol D.D., and Vögtle F. (Eds). Comprehensive Supramolecular Chemistry Vol. 6 (1996), Elsevier, Oxford Chapter 6
40. Miyata M., Sada K., and Yoswathananont N. In: Atwood J.L., and Steed J.W. (Eds). Encyclopedia of Supramolecular Chemistry (2004), Marcel Dekker, New York, NY 441
41. Yoswathananont N., Miyata Mi., Nakano K., and Sada K. Separation of Isomers and Enantiomers by Bile Acid Derivatives. In: Toda F., and Bishop R. (Eds). Separations and Reactions in Organic Supramolecular Chemistry (2004), Wiley, Hoboken, NJ 87-122
42. Miyata M., Shibakami M., and Takemoto K. J. Chem. Soc., Chem. Commun. (1988) 655-656
43. Kato K., Aburaya K., Miyake Y., Sada K., Tohnai N., and Miyata M. Chem. Commun. (2003) 2872-2873
44. For a recent review, see:. Bortolini O., Fantin G., and Fogagnolo M. Chirality 17 (2005) 121-130 and references therein
45. Herndon W.C. J. Chem. Educ. 44 (1967) 724-728
46. Miyata M., Shibakami M., Chirachanchai S., Takemoto K., Kasai N., and Miki K. Nature 343 (1990) 446-447
47. Nakano K., Sada K., Nakagawa K., Aburaya K., Yoswathananont N., Tohnai N., and Miyata M. Chem.-Eur. J. 11 (2005) 1725-1733
48. Anelli P.L., Lattuada L., and Uggeri F. Synth. Commun. 28 (1998) 109-117
49. Kato K., Inoue K., Tohnai N., and Miyata M. J. Inclusion Phenom. Macrocyc. Chem. 48 (2004) 61-67
50. Johnson P.L., and Schaefer J.P. Acta Crystallogr. B28 (1972) 3083-3088
51. Jones E.L., and Nassimbeni L.R. Acta Crystallogr. B46 (1990) 399-405
52. Miyata M., Shibakami M., Goonewardena W., and Takemoto K. Chem. Lett. (1987) 605-608
53. Speakman J.C. Struct. Bonding 12 (1972) 141-199
54. Novak A. Struct. Bonding 18 (1974) 177-216
55. Emsley J. Chem. Soc. Rev. 9 (1980) 91-124
56. Gilli G. Fundamentals of Crystallography. In: Giacovazzo C. (Ed) (1992), Oxford University Press, Oxford, UK Chapter 7
57. Gilli P., Bertolasi V., Ferretti V., and Gilli G. J. Am. Chem. Soc. 116 (1994) 909-915
58. Görbitz C.H. Acta Crystallogr. B45 (1989) 390-395
59. Aakeröy C.B., and Seddon K.R. Chem. Soc. Rev. 22 (1993) 397-407
60. Ward M.D. Chem. Commun. (2005) 5838-5842
61. Aakeröy C.B., Beatty A.M., and Lorimer K.R. Struct. Chem. 10 (1999) 229-242
62. Lida T., Shinohara T., Momose T., Tamura T., Matsumoto T., Nambara T., and Chang F.C. Synthesis 12 (1986) 998-1004
63. Schneider S., Schramm U., Schreyer A., Buscher H.-P., Gerok W., and Kurz G. J. Lipid Res. 32 (1991) 1755-1767
64. Blessing R.H. Acta Crystallogr. A51 (1995) 33-38
65. All software and sources of the scattering factors are contained in the SHELXTL (version 5.1) program library (G. Sheldrick, Bruker Analytical X-ray Systems, Madison, WI).