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Volumn 13, Issue 9, 2007, Pages 2717-2728

A combined computational and experimental approach for the analysis of the enantioselective potential of a new macrocyclic receptor for N-protected α-amino acids

(4) Ragusa, Andrea a,c Hayes, Joseph M b,d Light, Mark E a Kilburn, Jeremy D a

a UNIVERSITY OF SOUTHAMPTON (United Kingdom)

b Anterio Consult and Research GmbH (Germany)

c CSIC (Spain)

d UNIVERSITAT AUTÒNOMA DE BARCELONA (Spain)

Author keywords

Enantioselectivity host guest systems; Molecular modeling; Molecular recognition; Receptors

Indexed keywords

ALGORITHMS; CRYSTAL STRUCTURE; FREE ENERGY; MOLECULAR MODELING; MOLECULAR RECOGNITION; SOLVENTS;

ENANTIOSELECTIVITY HOST-GUEST SYSTEMS; MODE INTEGRATION ALGORITHM (MINTA);

AMINO ACIDS;

EID: 34250785219 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.200601289 Document Type: Article

Times cited : (16)

References (57)

1
- 25444502909
- A. Ragusa, S. Rossi, J. M. Hayes, M. Stein, J. D. Kilburn, Chem. Eur. J. 2005, 77, 5674-5688.
- (2005) Chem. Eur. J , vol.77 , pp. 5674-5688
- Ragusa, A.¹ Rossi, S.² Hayes, J.M.³ Stein, M.⁴ Kilburn, J.D.⁵

2
- 2342465506
- J. M. Hayes, M. Stein, J. Weiser, J. Phys. Chem. A 2004, 108, 3572-3580.
- (2004) J. Phys. Chem. A , vol.108 , pp. 3572-3580
- Hayes, J.M.¹ Stein, M.² Weiser, J.³

3
- 9144227552
- R. H. Henchman, J. D. Kilburn, D. L. Turner, J. W. Essex, J. Phys. Chem. B 2004, 705, 17571-17582.
- (2004) J. Phys. Chem. B , vol.705 , pp. 17571-17582
- Henchman, R.H.¹ Kilburn, J.D.² Turner, D.L.³ Essex, J.W.⁴

4
- 3242733866
- A. del Rio, J. M. Hayes, M. Stein, P. Piras, C. Roussel, Chirality 2004, 16, S1-S11.
- (2004) Chirality , vol.16
- del Rio, A.¹ Hayes, J.M.² Stein, M.³ Piras, P.⁴ Roussel, C.⁵

5
- 0035847244
- K. B. Lipkowitz, J. Chromatogr, A 2001, 906, 417-442.
- (2001) J. Chromatogr, A , vol.906 , pp. 417-442
- Lipkowitz, K.B.¹

6
- 0023936327
- R. L. DesJarlais, R. P. Sheridan, G. L. Seibel, J. S. Dixon, I. D. Kuntz, R. Venkataraghavan, J. Med. Chem. 1988, 37, 722-729.
- (1988) J. Med. Chem , vol.37 , pp. 722-729
- DesJarlais, R.L.¹ Sheridan, R.P.² Seibel, G.L.³ Dixon, J.S.⁴ Kuntz, I.D.⁵ Venkataraghavan, R.⁶

7
- 34250720094
- Glide 2.7, Schrödinger, LLC, New York, NY, 2003.
- Glide 2.7, Schrödinger, LLC, New York, NY, 2003.

8
- 0031181346
- C. McMartin, R. S. Bohacek, Comput.-Aided Mol. Des. 1997, 77, 333-344.
- (1997) Comput.-Aided Mol. Des , vol.77 , pp. 333-344
- McMartin, C.¹ Bohacek, R.S.²

9
- 34250708553
- D. S. Goodsell, A. Olsen, J. Protein Chem. 1990, 9, 195-202.
- (1990) J. Protein Chem , vol.9 , pp. 195-202
- Goodsell, D.S.¹ Olsen, A.²

10
- 36849122972
- R. W. Zwanzig, J. Chem. Phys. 1954, 22, 1420-1426.
- (1954) J. Chem. Phys , vol.22 , pp. 1420-1426
- Zwanzig, R.W.¹

11
- 7044239742
- P. Kollman, Chem. Rev. 1993, 93, 2395-2417.
- (1993) Chem. Rev , vol.93 , pp. 2395-2417
- Kollman, P.¹

12
- 36749107989
- M. R. Mruzik, F. F. Abraham, D. E. Schreiber, G. M. Pound, J. Chem. Phys. 1976, 64, 481-491.
- (1976) J. Chem. Phys , vol.64 , pp. 481-491
- Mruzik, M.R.¹ Abraham, F.F.² Schreiber, D.E.³ Pound, G.M.⁴

13
- 0031337279
- I. Kolossváry, J. Phys. Chem. A 1997, 707, 9900-9905.
- (1997) J. Phys. Chem. A , vol.707 , pp. 9900-9905
- Kolossváry, I.¹

14
- 34250766253
- US Patent Serial
- No. 08/940, 145, Mode Integration MINTA, Method and Apparatus for Selecting a Molecule Based on Conformational Free Energy, filed September 29, 1997
- I. Kolossváry, US Patent Serial No. 08/940, 145, Mode Integration (MINTA): Method and Apparatus for Selecting a Molecule Based on Conformational Free Energy, filed September 29, 1997.
- Kolossváry, I.¹

15
- 0031079364
- M. S. Head, J. A. Given, M. K. Gilson, J. Phys. Chem. A 1997, 707, 1609-1618.
- (1997) J. Phys. Chem. A , vol.707 , pp. 1609-1618
- Head, M.S.¹ Given, J.A.² Gilson, M.K.³

16
- 0030694573
- I. Kolossváry, J. Am. Chem. Soc. 1997, 779, 10233-10234.
- (1997) J. Am. Chem. Soc , vol.779 , pp. 10233-10234
- Kolossváry, I.¹

17
- 0026620937
- D. Q. McDonald, W. C. Still, Tetrahedron Lett. 1992, 33, 7747-7750.
- (1992) Tetrahedron Lett , vol.33 , pp. 7747-7750
- McDonald, D.Q.¹ Still, W.C.²

18
- 0000539622
- P. A. Kollman, Acc. Chem. Res. 1996, 29, 461-469.
- (1996) Acc. Chem. Res , vol.29 , pp. 461-469
- Kollman, P.A.¹

19
- 0008025298
- A. E. Mark, S. P. van Helden, P. E. Smith, L. H. M. Janssen, W. F. van Gunsteren, J. Am. Chem. Soc. 1994, 776, 6293-6302.
- (1994) J. Am. Chem. Soc , vol.776 , pp. 6293-6302
- Mark, A.E.¹ van Helden, S.P.² Smith, P.E.³ Janssen, L.H.M.⁴ van Gunsteren, W.F.⁵

20
- 0037165453
- a) M. J. Potter, M. K. Gilson, J. Phys. Chem. A 2002, 700, 563-566;
- (2002) J. Phys. Chem. A , vol.700 , pp. 563-566
- Potter, M.J.¹ Gilson, M.K.²

21
- 0037473066
- b) C. -E. Chang, M. J. Potter, M. K. Gilson, J. Phys. Chem. B 2003, 707, 1048-1055.
- (2003) J. Phys. Chem. B , vol.707 , pp. 1048-1055
- Chang, C.-E.¹ Potter, M.J.² Gilson, M.K.³

22
- 33748364753
- A. Ragusa, J. M. Hayes, M. E. Light, J. D. Kilburn, Eur. J. Org. Chem. 2006, 76, 3545-3549.
- (2006) Eur. J. Org. Chem , vol.76 , pp. 3545-3549
- Ragusa, A.¹ Hayes, J.M.² Light, M.E.³ Kilburn, J.D.⁴

23
- 30444431852
- a) J. R. Maple, Y. Cao, W. Damm, T. A. Halgren, G. A. Kaminski, L. Y. Zhang, R. A. Friesner, J. Chem. Theory Comput. 2005, 7, 694-715;
- (2005) J. Chem. Theory Comput , vol.7 , pp. 694-715
- Maple, J.R.¹ Cao, Y.² Damm, W.³ Halgren, T.A.⁴ Kaminski, G.A.⁵ Zhang, L.Y.⁶ Friesner, R.A.⁷

24
- 18744402303
- b) V. M. Anisimov, G. Lamoureux, I. V. Vorobyov, N. Huang, B. Roux, A. D. MacKerrell, J. Chem. Theory Comput. 2005, 7, 153-168;
- (2005) J. Chem. Theory Comput , vol.7 , pp. 153-168
- Anisimov, V.M.¹ Lamoureux, G.² Vorobyov, I.V.³ Huang, N.⁴ Roux, B.⁵ MacKerrell, A.D.⁶

25
- 4043057278
- c) S. Patel, C. L. Brooks, J. Comput. Chem. 2004, 25, 1504-1514;
- (2004) J. Comput. Chem , vol.25 , pp. 1504-1514
- Patel, S.¹ Brooks, C.L.²

26
- 18744395785
- d) L. R. Olano, S. W. Rick, J. Comput. Chem. 2005, 26, 699-707;
- (2005) J. Comput. Chem , vol.26 , pp. 699-707
- Olano, L.R.¹ Rick, S.W.²

27
- 33746597823
- e) S. Patel, C. L. Brooks, Molec. Simul. 2006, 32, 231-249.
- (2006) Molec. Simul , vol.32 , pp. 231-249
- Patel, S.¹ Brooks, C.L.²

28
- 25444486501
- S. Rossi, G. M. Kyne, D. L. Turner, N. J. Wells, J. D. Kilburn, Angew. Chem. 2002, 114, 4407-4409;
- (2002) Angew. Chem , vol.114 , pp. 4407-4409
- Rossi, S.¹ Kyne, G.M.² Turner, D.L.³ Wells, N.J.⁴ Kilburn, J.D.⁵

29
- 85047696169
- Angew. Chem. Int. Ed. 2002, 41, 4233-4236.
- (2002) Chem. Int. Ed , vol.41 , pp. 4233-4236
- Angew¹

30
- 0000161175
- C. A. Hunter, D.H. Purvis, Angew. Chem. 1992, 104, 779-782;
- (1992) Angew. Chem , vol.104 , pp. 779-782
- Hunter, C.A.¹ Purvis, D.H.²

31
- 33748597066
- Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795.
- (1992) Angew. Chem. Int. Ed. Engl , vol.31 , pp. 792-795

32
- 34250758685
- Single-crystal X-ray diffraction study: Data were collected on a Bruker Nonius KappaCCD mounted at the window of an Mo rotating anode. Standard data collection and reduction procedures were followed. Crystal data for 1: C 30H27.5N6.5O2S, Mr, 543.15, T= 120(2) K, orthorhombic, space group P21212 1, a= 11.7527(2, b= 13.0264(2, c= 35.5767(9) Å, V=5446.63(19) Å3, ρcaled= 1.325 gcm-3, μ= 0.16 mm-1, Z=8, 27591 reflections collected, 11764 independent reflections (Rint=0.1051, final R indices [I>2ρI, R1, 0.0750, wR2, 0.1196, K indices all data, A1, 0.2370. wR2, 0.1607. CCDC-609671 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- 2 = 0.1607. CCDC-609671 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

33
- 0034742734
- G. M. Kyne, M. E. Light, M. B. Hursthouse, J. de Mendoza, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2001, 1258-1263.
- (2001) J. Chem. Soc. Perkin Trans. 1 , pp. 1258-1263
- Kyne, G.M.¹ Light, M.E.² Hursthouse, M.B.³ de Mendoza, J.⁴ Kilburn, J.D.⁵

34
- 34250729805
- all binding data from NMR titration experiments are provided in the Supporting Information
- A. P. Bisson, C. A. Hunter, J. C. Morales, K. Young, Chem. Eur. J. 1998, 4, 485-851; all binding data from NMR titration experiments are provided in the Supporting Information.
- (1998) Chem. Eur. J , vol.4 , pp. 485-851
- Bisson, A.P.¹ Hunter, C.A.² Morales, J.C.³ Young, K.⁴

35
- 0025343507
- D. B. Smithrud, F. Diederich, J. Am. Chem. Soc. 1990, 112, 339-343.
- (1990) J. Am. Chem. Soc , vol.112 , pp. 339-343
- Smithrud, D.B.¹ Diederich, F.²

36
- 84986437005
- F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 77, 440-467.
- (1990) J. Comput. Chem , vol.77 , pp. 440-467
- Mohamadi, F.¹ Richards, N.G.J.² Guida, W.C.³ Liskamp, R.⁴ Lipton, M.⁵ Caufield, C.⁶ Chang, G.⁷ Hendrickson, T.⁸ Still, W.C.⁹

37
- 34250786786
- MacroModel version 8.1, Schrödinger, LLC, New York, NY, 2003
- MacroModel version 8.1, Schrödinger, LLC, New York, NY, 2003.

38
- 0043162336
- G. Chang, W. C. Guida, W. C. Still, J. Am. Chem. Soc. 1989, 111, 4379-4386;
- (1989) J. Am. Chem. Soc , vol.111 , pp. 4379-4386
- Chang, G.¹ Guida, W.C.² Still, W.C.³

39
- 0007793280
- M. Saunders, K. N. Houk, Y. D. Wu, W. C. Still, M. Lipton, G. Chang, W. C. Guida, W. C. Still, J. Am. Chem. Soc. 1990, 772, 1419-1427.
- (1990) J. Am. Chem. Soc , vol.772 , pp. 1419-1427
- Saunders, M.¹ Houk, K.N.² Wu, Y.D.³ Still, W.C.⁴ Lipton, M.⁵ Chang, G.⁶ Guida, W.C.⁷ Still, W.C.⁸

40
- 0344778061
- W. C. Still, A. Tempczyk, R. C. Cawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 772, 6127-6129.
- (1990) J. Am. Chem. Soc , vol.772 , pp. 6127-6129
- Still, W.C.¹ Tempczyk, A.² Cawley, R.C.³ Hendrickson, T.⁴

41
- 0001229337
- J. Weiser, A. A. Weiser, P. S. Shenkin, W. C. Still, J. Comput. Chem. 1998, 19, 797-808.
- (1998) J. Comput. Chem , vol.19 , pp. 797-808
- Weiser, J.¹ Weiser, A.A.² Shenkin, P.S.³ Still, W.C.⁴

42
- 0000408363
- J. Weiser, P. S. Shenkin, W. C. Still, J. Comput. Chem. 1999, 20, 217-230, 586-596.
- (1999) J. Comput. Chem , vol.20
- Weiser, J.¹ Shenkin, P.S.² Still, W.C.³

43
- 0037571112
- T. A. Halgren, J. Comput. Chem. 1996, 77, 490-519, 520-552, 553-586, 616-641;
- T. A. Halgren, J. Comput. Chem. 1996, 77, 490-519, 520-552, 553-586, 616-641;

44
- 0001061464
- T. A. Halgren, R. B. Nachbar, J. Comput. Chem. 1996, 17, 587-615.
- (1996) J. Comput. Chem , vol.17 , pp. 587-615
- Halgren, T.A.¹ Nachbar, R.B.²

45
- 5544242529
- T. A. Halgren, J. Comput. Chem. 1999, 20, 720-729, 730-748.
- (1999) J. Comput. Chem , vol.20
- Halgren, T.A.¹

46
- 0142236572
- I. Kolossváry, W. C. Guida, J. Am. Chem. Soc. 1996, 118, 5011-5019.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 5011-5019
- Kolossváry, I.¹ Guida, W.C.²

47
- 0242669291
- P. A. Greenidge, S. A. M. Merette, R. Beck, G. Dodson, C. A. Goodwin, M. F. Scully, J. Spencer, J. Weiser, J. J. Deadman, J. Med. Chem. 2003, 40, 1293-1305.
- (2003) J. Med. Chem , vol.40 , pp. 1293-1305
- Greenidge, P.A.¹ Merette, S.A.M.² Beck, R.³ Dodson, G.⁴ Goodwin, C.A.⁵ Scully, M.F.⁶ Spencer, J.⁷ Weiser, J.⁸ Deadman, J.J.⁹

48
- 0000147236
- I. Kolossváry, W. C. Guida, J. Comput. Chem. 1999, 20, 1671-1684.
- (1999) J. Comput. Chem , vol.20 , pp. 1671-1684
- Kolossváry, I.¹ Guida, W.C.²

49
- 84973610749
- F. Guarnieri, W. C. Still, J. Comput. Chem. 1994, 75, 1302-1310.
- (1994) J. Comput. Chem , vol.75 , pp. 1302-1310
- Guarnieri, F.¹ Still, W.C.²

50
- 0000889732
- D. Q. McDonald, W. C. Still, J. Am. Chem. Soc. 1994, 116, 11550-11553.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 11550-11553
- McDonald, D.Q.¹ Still, W.C.²

51
- 34250753929
- MacroModel 8.5 Reference Manual, Schrödinger, LLC, New York, NY, 2003, p. 152.
- MacroModel 8.5 Reference Manual, Schrödinger, LLC, New York, NY, 2003, p. 152.

52
- 0030730747
- J. L. Sessler, A. Andrievsky, V. Král, V. Linch, J. Am. Chem. Soc. 1997, 119, 9385-9392.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 9385-9392
- Sessler, J.L.¹ Andrievsky, A.² Král, V.³ Linch, V.⁴

53
- 84988112508
- J. W. Ponder, F. M. Richards, J. Comput. Chem. 1987, 8, 1016-1024.
- (1987) J. Comput. Chem , vol.8 , pp. 1016-1024
- Ponder, J.W.¹ Richards, F.M.²

54
- 34250719286
- www.chemfinder.com

55
- 34250761961
- E. Polak, G. Ribiere, Rev. Fr. Inform. Rech. Oper. 1969, 16-R1, 35-43.
- E. Polak, G. Ribiere, Rev. Fr. Inform. Rech. Oper. 1969, 16-R1, 35-43.

56
- 0029831680
- L. A. Kelley, S. P. Gardner, M. J. Sutcliffe, Protein Eng. 1996, 9, 1063-1065; http://neon.chem.le.ac.uk/nmr.clust/.
- (1996) Protein Eng , vol.9 , pp. 1063-1065
- Kelley, L.A.¹ Gardner, S.P.² Sutcliffe, M.J.³

57
- 34250751865
- New York, NY
- Jaguar 6.0, Schrödinger, LLC, New York, NY, 2003; www.schrodinger.com.
- (2003) Jaguar 6.0, Schrödinger, LLC

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