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5 kcal/mol of the lowest found minimum were kept and redundant
conformations were eliminated using a 0.50 A cutoff for maximum
atom deviation after superimposing all heavy atoms.
ꢁ
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The conformations were superimposed on
b-turns found in
proteins using SYBYL.23 The
b
-turn database consisted of 13,784 b-
turns, extracted from a representative set of crystallized proteins
using PDB_SELECT list23 from December 2003. The superimposed
atoms in the b-turns were Ca , Caiþ1, Cbiþ1, Caiþ2, Cbiþ2 and Caiþ3. The
i
corresponding superimposed atoms in the
in Fig. 1.
b-turn mimic are shown
4.3. Determination of X-ray structure of 14f
Crystallographic data (excluding structure factors) for the
structure 14f in this paper have been deposited with the Cambridge
Crystallographic Data Centre as supplementary publication CCDC
864858. Copies of the data can be obtained, free of charge, on ap-
plication to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax:
Program used to solve structure: SUPERFLIP (Palatinus, 2007);
program used to refine structure: SHELXL97 (Sheldrick, 1997);
molecular graphics: WinGX (Faruggia, 1998).
6. For recent examples, see: (a) Krasavin, M.; Parchinsky, V.; Shumsky, A.; Kon-
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U.; Burgess, K. J. Am. Chem. Soc. 2008, 130, 556e565; (g) Lomlim, L.; Einsiedel, J.;
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Verdie, P.; Subra, G.; Averland-Petit, M.-C.; Amblard, M.; Martinez, J. J. Comb.
3
ꢁ
Chem. 2008, 10, 869e874; (i) Lesma, G.; Colombo, A.; Sacchetti, A.; Silvani, A.
Tetrahedron Lett. 2008, 49, 7423e7425.
Crystal data for 14f C19H18N4O5, V¼3731.5 (13) A , Mr¼382.37,
ꢁ
Z¼8, orthorhombic, Pbcn, Cu K
a
radiation,
l
¼1.54178 A, a¼25.070
ꢀ
7. (a) Tomboly, C.; Ballet, S.; Feytens, D.; Kover, K. E.; Borics, A.; Lovas, S.; Al-
(5) A,
m
¼0.84 mmꢁ1, b¼10.591 (2) A, T¼213 K, c¼14.054 (3) A,
ꢁ
ꢁ
ꢁ
Khrasani, M.; Furst, Z.; Toth, G.; Benhye, S.; Tourwe, D. J. Med. Chem. 2008, 51,
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0.1ꢃ0.1ꢃ0.01 mm. Data collection: Image plate diffractometer 3025
independent reflections. Absorption correction: multi-scan, 1832
reflections with I >2
s
(I), Tmin¼0.514, Tmax¼1.000, Rint¼0.075,
11,666 measured reflections. Refinement: R[F2 >2
s
(F2)]¼0.109,
0 restraints wR(F2)¼0.333, H-atom parameters constrained, S¼1.12,
8. Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Biochim. Biophys. Acta 1973, 303,
211e229.
ꢁꢁ3
ꢁꢁ3
Drmax¼0.25 e A , 3025 reflections Drmin¼ꢁ0.21 e A , 254 pa-
rameters. A structure report can be found in the Supplementary
data.
9. (a) Ramachandran, G. N.; Venkatachalam, C. M. Biopolymers 1968, 6,
1255e1262; (b) Hutchinson, E. G.; Thornton, J. M. Protein Sci. 1994, 12,
2207e2216; (c) Richardson, J. S. Adv. Protein Chem. 1981, 34, 167e339.
10. (a) Vekemans, J.; Pollers-Wieers, C.; Hoornaert, G. J. Heterocycl. Chem. 1983, 20,
€
€
919e923; (b) Gising, J.; Ortqvist, P.; Sandstrom, A.; Larhed, M. Org. Biomol.
Chem. 2009, 7, 2809e2815.
Acknowledgements
11. (a) Ermolat’ev, D. S.; Mehta, V. P.; Van der Eycken, E. V. QSAR Comb. Sci. 2007, 26,
1266e1273; (b) Ermolat’ev, D. S.; Mehta, V. P.; Van der Eycken, E. V. Synlett
2007, 3117e3122; (c) Mehta, V. P.; Modha, S. G.; Ermolat’ev, D.; Van Hecke, K.;
Van Meervelt, L.; Van der Eycken, E. V. Aust. J. Chem. 2009, 62, 27e41.
The authors thank the F.W.O. (Fund for Scientific Research e
Flanders (Belgium)), the Swedish Research Council (VR) and the
Research Fund of the Katholieke Universiteit Leuven for financial
support to the laboratory. V.S.P. and M.T. thank the University of
Delhi under the ‘DU-DST Purse Grant’ for financial assistance. The
authors are thankful to Dr. Brice Kauffman of the IECB’s technology
platform (UMS 3033-US001) for the 3D structure determination
using X-ray diffraction.
€
ꢀ
12. (a) Ortqvist, P.; Gising, J.; Ehrenberg, A.; Vema, A.; Borg, A.; Karlen, A.; Larhed,
€
M.; Danielson, U. H.; Sandstrom, A. Bioorg. Med. Chem. 2010, 18, 6512e6525; (b)
Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043e6048.
13. Van Baelen, G.; Maes, B. U. W. Tetrahedron 2008, 64, 5604e5619.
14. Brennfuehrer, A.; Neumann, H.; Beller, M. Angew. Chem. 2009, 48, 4114e4133.
15. Because of the failure, these methods are not discussed in detail but the at-
tempted reaction conditions are specified in the experimental part.
16. Singh, B. K.; Cavalluzzo, C.; De Maeyer, M.; Debyser, Z.; Parmar, V. S.; Van der
Eycken, E. Eur. J. Org. Chem. 2009, 27, 4589e4592.
€
€
17. (a) Rosenstrom, U.; Skold, C.; Plouffe, B.; Beaudry, H.; Lindeberg, G.; Botros, M.;
Supplementary data
ꢀ
Nyberg, F.; Wolf, G.; Karlen, A.; Gallo-Payet, N.; Hallberg, A. J. Med. Chem. 2005,
48, 4009e4024; (b) Georgsson, J.; Skold, C.; Plouffe, B.; Lindeberg, G.; Botros,
M.; Larhed, M.; Nyberg, F.; Gallo-Payet, N.; Karlen, A.; Hallberg, A. J. Med.
Chem. 2005, 48, 6620e6631; (c) Rosenstrom, U.; Skold, C.; Lindeberg, G.;
€
Supplementary data associated with this article can be found, in
ꢀ
€
€
ꢀ
Botros, M.; Nyberg, F.; Karlen, A.; Hallberg, A. J. Med. Chem. 2006, 49,
6133e6137.
References and notes
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