C-H⋯O and other weak hydrogen bonds. From crystal engineering to virtual screening

Chemical Communications

Volumn , Issue 24, 2005, Pages 2995-3001

  Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN;

BIOMOLECULAR ELECTRONICS; CHEMICAL ENGINEERING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DRUG DESIGN; ELECTRON TRANSPORT; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; REVIEW;

EID: 21844471832     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504372g     Document Type: Review

References (49)

1. J. A. R. P. Sarma and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1987, 1195.
2. L. Leiserowitz, Acta Crystallogr., Sect. B, 1976, 32, 775.
3. G. R. Desiraju and B. N. Murty, Chem. Phys. Lett., 1987, 139, 360.
4. G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1989, 179.
5. V. R. Pedireddi and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1992, 988.
6. R. Taylor and O. Kennard. J. Am. Chem. Soc., 1982, 104, 5063.
7. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
8. (a) H. Bock, R. Dieneldt, H. Schödel and Z. Havlas, J. Chem. Soc., Chem. Commun., 1993, 1792;
9. (b) A. Cappelli, G. Giorgi, M. Anzini, S. Vomero, S. Ristori, C. Rossi and A. Donati, Chem. Eur. J., 2004, 10, 3177;
10. (c) G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1990, 454.
11. (a) S. S. Kuduva, D. C. Craig, A. Nangia and G. R. Desiraju, J. Am. Chem. Soc., 1999, 121, 1936;
12. (b) D. Das, R. K. R. Jetti, R. Boese and G. R. Desiraju, Cryst. Growth Des., 2003, 3, 675.
13. (a) P. G. Jones and F. Vancea, CrystEngComm, 2003, 5, 303;
14. (b) A. Anthony, M. Jaskólski, A. Nangia and G. R. Desiraju, Chem. Commun., 1998, 2537.
15. V. R. Thalladi, H.-C. Weiss, D. Bläser, R. Boese, A. Nangia and G. R. Desiraju, J. Am. Chem. Soc., 1998, 120, 8702.
16. F. Hof and F. Diederich, Chem. Commun., 2004, 484 and the references cited therein.
17. S. C. F. Kui, N. Zhu and M. C. W. Chan, Angew. Chem., Int. Ed., 2003, 42, 1628.
18. M. Nishio, CrystEngComm, 2004, 6, 130.
19. (a) P. Hobza and Z. Havlas, Chem. Rev., 2000, 100, 4253;
20. (b) A. J. Barnes, J. Mol. Struct., 2004, 704, 3.
21. D. Braga, J. Chem. Soc., Dalton Trans., 2000, 3705 and the references cited therein.
22. L. Brammer, in Crystal Design. Structure and Function, (Perspectives in Supramolecular Chemistry, vol. 7), ed. G. R. Desiraju, Wiley, Chichester, 2003, pp. 1-75.
23. Y. Gu, T. Kar and S. Scheiner, J. Am. Chem. Soc., 1999, 121, 9411.
24. T. Steiner and G. R. Desiraju, Chem. Commun., 1998, 891.
25. (a) G. R. Desiraju, Acc. Chem. Res., 2002, 35, 565;
26. (b) G. R. Desiraju, Curr. Sci., 2005, 88, 374.
27. (a) G. R. Desiraju and C. V. K. M. Sharma, J. Chem. Soc., Chem. Commun., 1991, 1239;
28. (b) M. A. Viswamitra, R. Radhakrishnan, J. Bandekar and G. R. Desiraju, J. Am. Chem. Soc., 1993, 115, 4868;
29. (c) P. K. Thallapally, A. K. Katz, H. L. Carrell and G. R. Desiraju, Chem. Commun., 2002, 344.
30. P. K. Thallapally, G. R. Desiraju, M. Bagieu-Beucher, R. Masse, C. Bourgogne and J.-F. Nicoud, Chem. Commun., 2002, 1052.
31. R. Thaimattam, X. Feng, J. A. R. P. Sarma, T. C. W. Mak and G. R. Desiraju, J. Am. Chem. Soc., 2001, 123, 4432.
32. C. V. K. Sharma and G. R. Desiraju, J. Chem. Soc., Perkin Trans. 2, 1994, 2345.
33. D. Laliberté, T. Maris and J. D. Wuest, CrystEngComm, 2005, 7, 158.
34. (a) Z. S. Derewenda, L. Lee and U. Derewenda, J. Mol. Biol., 1995, 252, 248;
35. (b) M. Wahl and M. Sundaralingam, Trends Biochem. Sci., 1997, 22, 97;
36. (c) T. Steiner, Acta Crystallogr., Sect. D, 1995, 51, 93.
37. R. Bhattacharyya and P. Chakrabarti, J. Mol. Biol., 2003, 331, 925.
38. T. Steiner and G. Koellner, J. Mol. Biol., 2001, 305, 535.
39. (a) B. P. Klaholz and D. Moras, Structure, 2002, 10, 1197;
40. (b) L. Jiang and L. Lai, J. Biol. Chem., 2002, 277, 37732;
41. (c) G. F. Fabiola, S. Krishnaswamy, V. Nagarajan and V. Pattabhi, Acta Crystallogr., Sect. D, 1997, 53, 316.
42. S. Sarkhel and G. R. Desiraju, Proteins, 2004, 54, 247.
43. A. C. Pierce, K. L. Sandretto and G. W. Bemis, Proteins, 2002, 49, 567.
44. J. C. Adrian and C. S. Wilcox, J. Am. Chem. Soc., 1992, 114, 1398.
45. V. Aparna, G. Rambabu, S. K. Panigrahi, J. A. R. P. Sarma and G. R. Desiraju, J. Chem. Inf. Model., 2005. DOI: 10.1021/ci049676u.
46. (a) S. Grüneberg, M. T. Stubbs and G. Klebe, J. Med. Chem., 2002, 45, 3588;
47. (b) P. D. Lyne, Drug Discovery Today, 2002, 7, 1047;
48. (c) K. H. Bleicher, H.-J. Böhm, K. Müller and A. I. Alanine, Nat. Rev. Drug Discovery, 2003, 2, 369.
49. J. Stamos, M. X. Sliwkowski and C. Eigenbrot, J. Biol. Chem., 2002, 48, 46265.