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Organic and Biomolecular Chemistry

Volumn 8, Issue 4, 2010, Pages 916-924

Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in β-turn peptides

(3) Sladojevich, Filippo a Guarna, Antonio a Trabocchi, Andrea a

a UNIVERSITY OF FLORENCE (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADAPTIVE BEHAVIOUR; AMIDE PROTON; COMPACT STRUCTURES; CONFORMATIONAL CHANGE; CONFORMATIONAL PREFERENCES; HETEROCYCLIC COMPOUND; INTRAMOLECULAR HYDROGEN; MORPHOLINES; NMR ANALYSIS; SOLUTION PHASE; SPECTROSCOPIC DATA;

AMIDES; HYDROGEN BONDS;

PEPTIDES;

MORPHOLINE; MORPHOLINE DERIVATIVE; PEPTIDE; PROLINE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MORPHOLINES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES; PROLINE; PROTEIN FOLDING; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 76249088543 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b913444a Document Type: Article

Times cited : (21)

References (37)

1
- 0024391832
- B. L. Sibanda T. L. Blundell J. M. Thornton J. Mol. Biol. 1989 206 759 777
- (1989) J. Mol. Biol. , vol.206 , pp. 759-777
- Sibanda, B.L.¹ Blundell, T.L.² Thornton, J.M.³

2
- 0021779081
- G. D. Rose L. M. Gierasch J. A. Smith Adv. Protein Chem. 1985 37 1 109
- (1985) Adv. Protein Chem. , vol.37 , pp. 1-109
- Rose, G.D.¹ Gierasch, L.M.² Smith, J.A.³

3
- 0026766974
- J. Rizo L. M. Gierasch Annu. Rev. Biochem. 1992 61 387 418
- (1992) Annu. Rev. Biochem. , vol.61 , pp. 387-418
- Rizo, J.¹ Gierasch, L.M.²

4
- 0030867016
- M. D. Ferguson J. P. Meara H. Nakanishi M. S. Lee M. Kahn Tetrahedron Lett. 1997 38 6961 6964
- (1997) Tetrahedron Lett. , vol.38 , pp. 6961-6964
- Ferguson, M.D.¹ Meara, J.P.² Nakanishi, H.³ Lee, M.S.⁴ Kahn, M.⁵

5
- 0001352986
- ed. A. Abell, JAI Press, Stamford, CT
- F. A. Etzkorn, J. M. Travins and S. A. Hart, in Advances in amino acid mimetics and peptidomimetics, ed., A. Abell, JAI Press, Stamford, CT, 1999, vol. 2, pp. 125-163
- (1999) Advances in Amino Acid Mimetics and Peptidomimetics , pp. 125-163
- Etzkorn, F.A.¹ Travins, J.M.² Hart In, S.A.³

6
- 43449130074
- L. Lomlim J. Einsiedel F. W. Heinemann K. Meyer P. Gmeiner J. Org. Chem. 2008 73 3608 3611
- (2008) J. Org. Chem. , vol.73 , pp. 3608-3611
- Lomlim, L.¹ Einsiedel, J.² Heinemann, F.W.³ Meyer, K.⁴ Gmeiner, P.⁵

7
- 36649013845
- J. Einsiedel H. Lanig R. Waibel P. Gmeiner J. Org. Chem. 2007 72 9102 9113
- (2007) J. Org. Chem. , vol.72 , pp. 9102-9113
- Einsiedel, J.¹ Lanig, H.² Waibel, R.³ Gmeiner, P.⁴

8
- 33645234177
- D. Blomberg P. Kreye C. Fowler K. Brickmann J. Kihlberg Org. Biomol. Chem. 2006 4 416 423
- (2006) Org. Biomol. Chem. , vol.4 , pp. 416-423
- Blomberg, D.¹ Kreye, P.² Fowler, C.³ Brickmann, K.⁴ Kihlberg, J.⁵

9
- 4644326924
- X. Gu J. Ying R. S. Agnes E. Navratilova P. Davis G. Stahl F. Porreca H. I. Yamamura V. J. Hruby Org. Lett. 2004 6 3285 3288
- (2004) Org. Lett. , vol.6 , pp. 3285-3288
- Gu, X.¹ Ying, J.² Agnes, R.S.³ Navratilova, E.⁴ Davis, P.⁵ Stahl, G.⁶ Porreca, F.⁷ Yamamura, H.I.⁸ Hruby, V.J.⁹

10
- 0036827529
- M. M. Fernández A. Diez M. Rubiralta E. Montenegro N. Casamitjana M. J. Kogan E. Giralt J. Org. Chem. 2002 67 7587 7599
- (2002) J. Org. Chem. , vol.67 , pp. 7587-7599
- Fernández, M.M.¹ Diez, A.² Rubiralta, M.³ Montenegro, E.⁴ Casamitjana, N.⁵ Kogan, M.J.⁶ Giralt, E.⁷

11
- 0037187386
- M. Eguchi R. Y. Shen J. P. Shea M. S. Lee M. Kahn J. Med. Chem. 2002 45 1395 1398
- (2002) J. Med. Chem. , vol.45 , pp. 1395-1398
- Eguchi, M.¹ Shen, R.Y.² Shea, J.P.³ Lee, M.S.⁴ Kahn, M.⁵

12
- 0035929452
- E. Alonso F. López-Ortiz C. Del Pozo E. Peralta A. Macías J. González J. Org. Chem. 2001 66 6333 6338
- (2001) J. Org. Chem. , vol.66 , pp. 6333-6338
- Alonso, E.¹ López-Ortiz, F.² Del Pozo, C.³ Peralta, E.⁴ MacÍas, A.⁵ González, J.⁶

13
- 0033534574
- M. J. Soth J. S. Nowick J. Org. Chem. 1999 64 276 281
- (1999) J. Org. Chem. , vol.64 , pp. 276-281
- Soth, M.J.¹ Nowick, J.S.²

14
- 0033565011
- Y. Feng M. Pattarawapan Z. Wang K. Burgess Org. Lett. 1999 1 121 124
- (1999) Org. Lett. , vol.1 , pp. 121-124
- Feng, Y.¹ Pattarawapan, M.² Wang, Z.³ Burgess, K.⁴

15
- 0031468514
- S. Krauthäuser L. A. Christianson D. R. Powell S. H. Gellman J. Am. Chem. Soc. 1997 119 11719 11720
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 11719-11720
- Krauthäuser, S.¹ Christianson, L.A.² Powell, D.R.³ Gellman, S.H.⁴

16
- 0029139422
- R. R. Gardner G.-B. Liang S. H. Gellman J. Am. Chem. Soc. 1995 117 3280 3281
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3280-3281
- Gardner, R.R.¹ Liang, G.-B.² Gellman, S.H.³

17
- 0028555379
- A. A. Virgilio J. A. Ellman J. Am. Chem. Soc. 1994 116 11580 11581
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 11580-11581
- Virgilio, A.A.¹ Ellman, J.A.²

18
- 0035914012
- M. Breznik S. Goli Grdadolnik G. Giester I. Leban D. Kikelj J. Org. Chem. 2001 66 7044 7050
- (2001) J. Org. Chem. , vol.66 , pp. 7044-7050
- Breznik, M.¹ Goli Grdadolnik, S.² Giester, G.³ Leban, I.⁴ Kikelj, D.⁵

19
- 41949119312
- M. Wiesner J. D. Revell H. Wennemers Angew. Chem., Int. Ed. 2008 47 1871 1874
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 1871-1874
- Wiesner, M.¹ Revell, J.D.² Wennemers, H.³

20
- 45549101074
- A. Berkessel Angew. Chem., Int. Ed. 2008 47 3677 3679
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3677-3679
- Berkessel, A.¹

21
- 38349112828
- E. A. Colby Davie S. M. Mennen Y. Xu S. J. Miller Chem. Rev. 2007 107 5759 5812
- (2007) Chem. Rev. , vol.107 , pp. 5759-5812
- Colby Davie, E.A.¹ Mennen, S.M.² Xu, Y.³ Miller, S.J.⁴

22
- 34548453212
- G. Peris C. E. Jakobsche S. J. Miller J. Am. Chem. Soc. 2007 129 8710 8711
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 8710-8711
- Peris, G.¹ Jakobsche, C.E.² Miller, S.J.³

23
- 33846912717
- B. R. Linton M. H. Reutershan C. M. Aderman E. A. Richardson K. R. Brownell C. W. Ashley C. A. Evans S. J. Miller Tetrahedron Lett. 2007 48 1993 1997
- (2007) Tetrahedron Lett. , vol.48 , pp. 1993-1997
- Linton, B.R.¹ Reutershan, M.H.² Aderman, C.M.³ Richardson, E.A.⁴ Brownell, K.R.⁵ Ashley, C.W.⁶ Evans, C.A.⁷ Miller, S.J.⁸

24
- 2442710268
- F. Formaggio A. Barazza A. Bertocco C. Toniolo Q. B. Broxterman B. Kaptein E. Brasola P. Pengo L. Pasquato P. Scrimin J. Org. Chem. 2004 69 3849 3856
- (2004) J. Org. Chem. , vol.69 , pp. 3849-3856
- Formaggio, F.¹ Barazza, A.² Bertocco, A.³ Toniolo, C.⁴ Broxterman, Q.B.⁵ Kaptein, B.⁶ Brasola, E.⁷ Pengo, P.⁸ Pasquato, L.⁹ Scrimin, P.¹⁰

25
- 0029931671
- T. S. Haque J. C. Little S. H. Gellman J. Am. Chem. Soc. 1996 118 6975 6985
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975-6985
- Haque, T.S.¹ Little, J.C.² Gellman, S.H.³

26
- 34249827601
- F. Sladojevich A. Trabocchi A. Guarna J. Org. Chem. 2007 72 4254 4257
- (2007) J. Org. Chem. , vol.72 , pp. 4254-4257
- Sladojevich, F.¹ Trabocchi, A.² Guarna, A.³

27
- 67649414746
- A. Trabocchi F. Sladojevich A. Guarna Chirality 2009 21 584 594
- (2009) Chirality , vol.21 , pp. 584-594
- Trabocchi, A.¹ Sladojevich, F.² Guarna, A.³

28
- 23944496639
- J. I. Levin J. M. Chen L. M. Laakso M. Du X. Du A. M. Venkatesan V. Sandanayaka A. Zask J. Xu W. Xu Y. Zhang J. S. Skotnicki Bioorg. Med. Chem. Lett. 2005 15 4345 4349
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4345-4349
- Levin, J.I.¹ Chen, J.M.² Laakso, L.M.³ Du, M.⁴ Du, X.⁵ Venkatesan, A.M.⁶ Sandanayaka, V.⁷ Zask, A.⁸ Xu, J.⁹ Xu, W.¹⁰ Zhang, Y.¹¹ Skotnicki, J.S.¹²

29
- 0033523954
- N. G. Almstead R. S. Bradley S. Pikul B. De M. G. Natchus Y. O. Taiwo F. Gu L. E. Williams B. A. Hynd M. J. Janusz C. M. Dunaway G. E. Mieling J. Med. Chem. 1999 42 4547 4562
- (1999) J. Med. Chem. , vol.42 , pp. 4547-4562
- Almstead, N.G.¹ Bradley, R.S.² Pikul, S.³ De, B.⁴ Natchus, M.G.⁵ Taiwo, Y.O.⁶ Gu, F.⁷ Williams, L.E.⁸ Hynd, B.A.⁹ Janusz, M.J.¹⁰ Dunaway, C.M.¹¹ Mieling, G.E.¹²

30
- 9644291524
- Given the connection of the stereochemistry of the herein reported threonine-derived cyclic amino acids to l-proline, d-amino acids were used in the peptide synthesis, so as to attain the corresponding heterochiral peptides. It must be taken into account that morpholine-based scaffolds as effective d-proline surrogates are obtained from d-threonine as the building block
- J. Chiba N. Machinaga T. Takashi A. Ejima G. Takayama M. Yokoyama A. Nakayama J. J. Baldwin E. McDonald K. W. Saionz R. Swanson Z. Hussain A. Wong Bioorg. Med. Chem. Lett. 2005 15 41 45
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 41-45
- Chiba, J.¹ MacHinaga, N.² Takashi, T.³ Ejima, A.⁴ Takayama, G.⁵ Yokoyama, M.⁶ Nakayama, A.⁷ Baldwin, J.J.⁸ McDonald, E.⁹ Saionz, K.W.¹⁰ Swanson, R.¹¹ Hussain, Z.¹² Wong, A.¹³

31
- 52649144883
- The irradiation of the corresponding proton H-6 in compound 1a did not result in any nOe interaction with H-2 (see Fig. S1 in the ESI)
- F. Sladojevich A. Trabocchi A. Guarna Org. Biomol. Chem. 2008 6 3328 3336
- (2008) Org. Biomol. Chem. , vol.6 , pp. 3328-3336
- Sladojevich, F.¹ Trabocchi, A.² Guarna, A.³

32
- 0033541110
- The hexapeptide Boc-d-Ala-d-Val-Pro-Gly-d-Leu-d-Val-OMe was prepared by standard solution-phase peptide chemistry
- R. R. Gardner G.-B. Liang S. H. Gellman J. Am. Chem. Soc. 1999 121 1806 1816
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1806-1816
- Gardner, R.R.¹ Liang, G.-B.² Gellman, S.H.³

33
- 0037571112
- T. A. Halgren J. Comput. Chem. 1996 17 490 519
- (1996) J. Comput. Chem. , vol.17 , pp. 490-519
- Halgren, T.A.¹

34
- 0011134241
- T. A. Halgren J. Comput. Chem. 1996 17 520 552
- (1996) J. Comput. Chem. , vol.17 , pp. 520-552
- Halgren, T.A.¹

35
- 0011143599
- T. A. Halgren J. Comput. Chem. 1996 17 553 586
- (1996) J. Comput. Chem. , vol.17 , pp. 553-586
- Halgren, T.A.¹

36
- 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

37
- 5244268272
- T. A. Halgren J. Comput. Chem. 1996 17 616 641
- (1996) J. Comput. Chem. , vol.17 , pp. 616-641
- Halgren, T.A.¹

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