Inclusion compounds of l,d-dipeptide with small sulfoxides: flexible sheet structure of (S)-phenylglycyl-(R)-phenylglycine

Tetrahedron

Volumn 63, Issue 40, 2007, Pages 9933-9938

  Akazome, Motohiro ^a   Hirabayashi, Atsushi ^a   Senda, Kyoko ^a   Ogura, Katsuyuki ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Crystal engineering; Dipeptides; Inclusion compounds; Molecular recognition; Sulfoxides

Indexed keywords

AMMONIA; DIPEPTIDE; PHENYLGLYCINE; PHENYLGLYCYLPHENYLGLYCINE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; ENANTIOMER; HYDROGEN BOND; MOLECULAR MODEL; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; THERMOGRAVIMETRY; X RAY CRYSTALLOGRAPHY; X RAY POWDER DIFFRACTION;

EID: 34547930902     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.061     Document Type: Article

References (44)

1. Akazome M., Hirabayashi A., Kataoka K., Nomura S., and Ogura K. Tetrahedron 61 (2005) 1107-1113
2. Akazome M., Hirabayashi A., and Ogura K. Tetrahedron 60 (2004) 12085-12093
3. Akazome M., Ueno Y., Ooiso H., and Ogura K. J. Org. Chem. 65 (2000) 68-76
4. Akazome M., Noguchi M., Tanaka O., Sumikawa A., Uchida T., and Ogura K. Tetrahedron 53 (1997) 8315-8322
5. Ogura K., Uchida T., Noguchi M., Minoguchi M., Murata A., Fujita M., and Ogata K. Tetrahedron Lett. 31 (1990) 3331-3334
6. Akazome M., Takahashi T., Sonobe R., and Ogura K. Tetrahedron 58 (2002) 8857-8861
7. Akazome M., Takahashi T., Sonobe R., and Ogura K. Supramol. Chem. 13 (2001) 109-136
8. Akazome M., Takahashi T., and Ogura K. J. Org. Chem. 64 (1999) 2293-2300
9. Akazome M., Yanagita Y., Sonobe R., and Ogura K. Bull. Chem. Soc. Jpn. 70 (1997) 2823-2827
10. Akazome M., Sumikawa A., Sonobe R., and Ogura K. Chem. Lett. (1996) 995-996
11. Recent reviews on peptide helices and tubes:
12. Bong D.T., Clark T.D., Granja J.R., and Ghadiri M.R. Angew. Chem., Int. Ed. 40 (2001) 988-1011
13. Karle I.L. Acc. Chem. Res. 32 (1999) 693-701
14. Di Blasio B., Benedetti E., Pavone V., Pedone C., Spiniello O., and Lorenzi G.P. Biopolymers 28 (1989) 193-201
15. Di Blasio B., Benedetti E., Pavone V., Pedone C., Gerber C., and Lorenzi G.P. Biopolymers 28 (1989) 203-214
16. Benedetti E., Di Blasio B., Pedone C., Spiniello O., Lorenzi G.P., Tomasic L., and Gramlich V.A. Nature 282 (1979) 630
17. Hartgerink J.D., Granja J.R., Milligan R.A., and Ghadiri M.R. J. Am Chem. Soc. 118 (1996) 43-50
18. Ghadiri M.R., Granja J.R., Milligan R.A., McRee D.E., and Khazanovich N. Nature 366 (1993) 324-327
19. Pavone V., Benedetti E., Di Blasio B., Lombardi A., Pedone C., Tomasic L., and Lorenzi G.P. Biopolymers 28 (1989) 215-223
20. Akazome M., Senda K., and Ogura K. J. Org. Chem. 67 (2002) 8885-8889
21. Optical resolution of alkyl sulfoxides using inclusion phenomena has been already reported.
22. Toda F., Tanaka K., and Okada T. J. Chem. Soc., Chem. Commun. (1995) 639-640
23. Toda F., Tanaka K., and Mak T.C.W. Chem. Lett. (1984) 2085-2088
24. Toda F., Tanaka K., and Nagamatsu S. Tetrahedron Lett. 25 (1984) 4929-4932
25. Arad-Yellin R., Green B.S., Knossow M., and Tsoucaris G. J. Am. Chem. Soc. 105 (1983) 4561-4571
26. Allemand J., and Gredil R. Acta Crystallogr. B38 (1984) 2312-2315
27. Pauling L. The Nature of the Chemical Bond (1960), Cornell Univ, New York, NY p 260
28. Takahashi H., Tsuboyama S., Umezawa Y., Honda K., and Nishio M. Tetrahedron 56 (2000) 6185-6191
29. Tsuzuki S., Honda K., Uchimura T., Mikami M., and Tanabe K. J. Am. Chem. Soc. 122 (2000) 3746-3753
30. Kinbara K., Sakai K., Hashimoto Y., Nohira H., and Saigo K. J. Am. Chem. Soc. 118 (1996) 3441-3449
31. Kinbara K., Sakai K., Hashimoto Y., Nohira H., and Saigo K. J. Chem. Soc., Perkin Trans. 2 (1996) 2615-2622
32. Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Chem. Soc., Perkin Trans. 2 (2001) 651-668
33. Swift J.A., Pal R., and McBride J.M. J. Am Chem. Soc. 120 (1998) 96-104
34. Lewis F.D., Yang J.-S., and Stern C.L. J. Am Chem. Soc. 118 (1996) 12029-13037
35. Hunter C.A., and Sanders J.K.M. J. Am Chem. Soc. 112 (1990) 5525-5534
36. Desiraju G.R., and Gavezzotti A. J. Chem. Soc., Chem. Commun. (1989) 621-623
37. König W., and Geiger R. Chem. Ber. 103 (1970) 788-798
38. Doyle F.P., Fosker G.R., Nayler J.H., and Smith H. J. Chem. Soc. (1962) 1440-1445
39. Zervas L., Winitz M., and Greenstein J.P. J. Org. Chem. 22 (1957) 1515-1521
40. Yabuuchi T., and Kusumi T. J. Am. Chem. Soc. 121 (1999) 10646-10647
41. Altomare A., Cascarno G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G., and Camalli M. J. Appl. Crystallogr. 27 (1994) 435
42. Sheldrick G.M. Acta Crystallogr. A46 (1990) 467-473
43. Mackay S., Edwards C., Henderson A., Gilmoer C., Stweart N., Shankland K., and Donald A. maXus (1999), University of Glasgow, Scotland, UK
44. Sheldrick G.M. SHELXTL Version 5.10 (1997), Bruker AXS, Madison, WI