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Organic and Biomolecular Chemistry

Volumn 10, Issue 3, 2012, Pages 640-651

β-Phenylproline: The high β-turn forming propensity of proline combined with an aromatic side chain

(4) Fatás, Paola a Jiménez, Ana I a Calaza, M Isabel a Cativiela, Carlos a

a CSIC (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC GROUP; AROMATIC SIDE CHAINS; CARBONYL GROUPS; CONFORMATIONAL DIFFERENCES; DIPEPTIDE; HOMOCHIRAL; PHENYL SUBSTITUENTS; PHENYLALANINE RESIDUES; PYRROLIDINE RINGS; STERIC REPULSIONS; TRANS CONFIGURATION;

AROMATIC COMPOUNDS; AROMATIZATION; PEPTIDES; X RAY DIFFRACTION ANALYSIS;

AMINO ACIDS;

5 PHENYL PROLINE; 5-PHENYL PROLINE; DRUG DERIVATIVE; OLIGOPEPTIDE; PROLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; SPECTROSCOPY; STEREOISOMERISM; X RAY DIFFRACTION;

MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PROLINE; SPECTRUM ANALYSIS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; X-RAY DIFFRACTION;

EID: 84055224127 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c1ob06561k Document Type: Article

Times cited : (12)

References (59)

1
- 84890590823
- ed., John Wiley & Sons, Chichester
- Peptide and Protein Design for Biopharmaceutical Applications, ed., K. J. Jensen, John Wiley & Sons, Chichester, 2009
- (2009) Peptide and Protein Design for Biopharmaceutical Applications
- Jensen, K.J.¹

2
- 36849057990
- ed., Wiley-VCH, Weinheim, For reviews, see
- Foldamers: Structure, Properties, and Applications, ed., S. Hecht, and, I. Huc, Wiley-VCH, Weinheim, 2007
- (2007) Foldamers: Structure, Properties, and Applications
- Hecht, S.¹ Huc, I.²

3
- 80052047442
- K. Estieu-Gionnet G. Guichard Expert Opin. Drug Discovery 2011 6 937 963
- (2011) Expert Opin. Drug Discovery , vol.6 , pp. 937-963
- Estieu-Gionnet, K.¹ Guichard, G.²

4
- 79960304253
- C. Tomasini G. Angelici N. Castellucci Eur. J. Org. Chem. 2011 3648 3669
- (2011) Eur. J. Org. Chem. , pp. 3648-3669
- Tomasini, C.¹ Angelici, G.² Castellucci, N.³

5
- 79956128878
- G. Guichard I. Huc Chem. Commun. 2011 47 5933 5941
- (2011) Chem. Commun. , vol.47 , pp. 5933-5941
- Guichard, G.¹ Huc, I.²

6
- 57349134690
- W. S. Horne S. H. Gellman Acc. Chem. Res. 2008 41 1399 1408
- (2008) Acc. Chem. Res. , vol.41 , pp. 1399-1408
- Horne, W.S.¹ Gellman, S.H.²

7
- 57149097169
- D. Seebach J. Gardiner Acc. Chem. Res. 2008 41 1366 1375
- (2008) Acc. Chem. Res. , vol.41 , pp. 1366-1375
- Seebach, D.¹ Gardiner, J.²

8
- 57349171593
- J. Chatterjee C. Gilon A. Hoffman H. Kessler Acc. Chem. Res. 2008 41 1331 1342
- (2008) Acc. Chem. Res. , vol.41 , pp. 1331-1342
- Chatterjee, J.¹ Gilon, C.² Hoffman, A.³ Kessler, H.⁴

9
- 39149110644
- P. Maity B. König Biopolymers (Pept. Sci.) 2008 90 8 27
- (2008) Biopolymers (Pept. Sci.) , vol.90 , pp. 8-27
- Maity, P.¹ König, B.²

10
- 33644583896
- D. Seebach D. F. Hook A. Glättli Biopolymers (Pept. Sci.) 2006 84 23 37
- (2006) Biopolymers (Pept. Sci.) , vol.84 , pp. 23-37
- Seebach, D.¹ Hook, D.F.² Glättli, A.³

11
- 1942531292
- P. Mathur S. Ramakumar V. S. Chauhan Biopolymers (Pept. Sci.) 2004 76 150 161
- (2004) Biopolymers (Pept. Sci.) , vol.76 , pp. 150-161
- Mathur, P.¹ Ramakumar, S.² Chauhan, V.S.³

12
- 0035552035
- C. Toniolo M. Crisma F. Formaggio C. Peggion Biopolymers (Pept. Sci.) 2001 60 396 419
- (2001) Biopolymers (Pept. Sci.) , vol.60 , pp. 396-419
- Toniolo, C.¹ Crisma, M.² Formaggio, F.³ Peggion, C.⁴

13
- 0035471131
- J. Venkatraman S. C. Shankaramma P. Balaram Chem. Rev. 2001 101 3131 3152
- (2001) Chem. Rev. , vol.101 , pp. 3131-3152
- Venkatraman, J.¹ Shankaramma, S.C.² Balaram, P.³

14
- 0035471135
- R. P. Cheng S. H. Gellman W. F. DeGrado Chem. Rev. 2001 101 3219 3232
- (2001) Chem. Rev. , vol.101 , pp. 3219-3232
- Cheng, R.P.¹ Gellman, S.H.² Degrado, W.F.³

15
- 0035542909
- D. J. Hill M. J. Mio R. B. Prince T. S. Hughes J. S. Moore Chem. Rev. 2001 101 3893 4011
- (2001) Chem. Rev. , vol.101 , pp. 3893-4011
- Hill, D.J.¹ Mio, M.J.² Prince, R.B.³ Hughes, T.S.⁴ Moore, J.S.⁵

16
- 0034994293
- P. Chakrabarti D. Pal Prog. Biophys. Mol. Biol. 2001 76 1 102
- (2001) Prog. Biophys. Mol. Biol. , vol.76 , pp. 1-102
- Chakrabarti, P.¹ Pal, D.²

17
- 0025890946
- M. W. MacArthur J. M. Thornton J. Mol. Biol. 1991 218 397 412
- (1991) J. Mol. Biol. , vol.218 , pp. 397-412
- MacArthur, M.W.¹ Thornton, J.M.²

18
- 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

19
- 66149116389
- C. Armishaw A. A. Jensen T. Balle R. J. Clark K. Harpsøe C. Skonberg T. Liljefors K. Strømgaard J. Biol. Chem. 2009 284 9498 9512
- (2009) J. Biol. Chem. , vol.284 , pp. 9498-9512
- Armishaw, C.¹ Jensen, A.A.² Balle, T.³ Clark, R.J.⁴ Harpsøe, K.⁵ Skonberg, C.⁶ Liljefors, T.⁷ Strømgaard, K.⁸

20
- 40749144390
- J. A. Tran F. C. Tucci M. Arellano W. Jiang C. W. Chen D. Marinkovic B. A. Fleck J. Wen A. C. Foster C. Chen Bioorg. Med. Chem. Lett. 2008 18 1931 1938
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 1931-1938
- Tran, J.A.¹ Tucci, F.C.² Arellano, M.³ Jiang, W.⁴ Chen, C.W.⁵ Marinkovic, D.⁶ Fleck, B.A.⁷ Wen, J.⁸ Foster, A.C.⁹ Chen, C.¹⁰

21
- 33845968012
- E. F. Rosloniec T. Brandstetter S. Leyer F.-W. Schwaiger Z. A. Nagy J. Autoimmun. 2006 27 182 195
- (2006) J. Autoimmun. , vol.27 , pp. 182-195
- Rosloniec, E.F.¹ Brandstetter, T.² Leyer, S.³ Schwaiger, F.-W.⁴ Nagy, Z.A.⁵

22
- 1542725948
- M. Cai C. Cai A. V. Mayorov C. Xiong C. M. Cabello V. A. Soloshonok J. R. Swift D. Trivedi V. J. Hruby J. Pept. Res. 2004 63 116 131
- (2004) J. Pept. Res. , vol.63 , pp. 116-131
- Cai, M.¹ Cai, C.² Mayorov, A.V.³ Xiong, C.⁴ Cabello, C.M.⁵ Soloshonok, V.A.⁶ Swift, J.R.⁷ Trivedi, D.⁸ Hruby, V.J.⁹

23
- 0033680378
- I. J. McFadyen K. Sobczyk-Kojiro M. J. Schaefer J. C. Ho J. R. Omnaas H. I. Mosberg J. R. Traynor J. Pharmacol. Exp. Ther. 2000 295 960 966
- (2000) J. Pharmacol. Exp. Ther. , vol.295 , pp. 960-966
- McFadyen, I.J.¹ Sobczyk-Kojiro, K.² Schaefer, M.J.³ Ho, J.C.⁴ Omnaas, J.R.⁵ Mosberg, H.I.⁶ Traynor, J.R.⁷

24
- 0034214403
- D. R. Bolin A. L. Swain R. Sarabu S. J. Berthel P. Gillespie N. J. S. Huby R. Makofske L. Orzechowski A. Perrotta K. Toth J. P. Cooper N. Jiang F. Falcioni R. Campbell D. Cox D. Gaizband C. J. Belunis D. Vidovic K. Ito R. Crowther U. Kammlott X. Zhang R. Palermo D. Weber J. Guenot Z. Nagy G. L. Olson J. Med. Chem. 2000 43 2135 2148
- (2000) J. Med. Chem. , vol.43 , pp. 2135-2148
- Bolin, D.R.¹ Swain, A.L.² Sarabu, R.³ Berthel, S.J.⁴ Gillespie, P.⁵ Huby, N.J.S.⁶ Makofske, R.⁷ Orzechowski, L.⁸ Perrotta, A.⁹ Toth, K.¹⁰ Cooper, J.P.¹¹ Jiang, N.¹² Falcioni, F.¹³ Campbell, R.¹⁴ Cox, D.¹⁵ Gaizband, D.¹⁶ Belunis, C.J.¹⁷ Vidovic, D.¹⁸ Ito, K.¹⁹ Crowther, R.²⁰ more..

25
- 0034697350
- Y. Tong Y. M. Fobian M. Wu N. D. Boyd K. D. Moeller J. Org. Chem. 2000 65 2484 2493
- (2000) J. Org. Chem. , vol.65 , pp. 2484-2493
- Tong, Y.¹ Fobian, Y.M.² Wu, M.³ Boyd, N.D.⁴ Moeller, K.D.⁵

26
- 0033052417
- F. Falcioni K. Ito D. Vidovic C. Belunis R. Campbell S. J. Berthel D. R. Bolin P. B. Gillespie N. Huby G. L. Olson R. Sarabu J. Guenot V. Madison J. Hammer F. Sinigaglia M. Steinmetz Z. A. Nagy Nat. Biotechnol. 1999 17 562 567
- (1999) Nat. Biotechnol. , vol.17 , pp. 562-567
- Falcioni, F.¹ Ito, K.² Vidovic, D.³ Belunis, C.⁴ Campbell, R.⁵ Berthel, S.J.⁶ Bolin, D.R.⁷ Gillespie, P.B.⁸ Huby, N.⁹ Olson, G.L.¹⁰ Sarabu, R.¹¹ Guenot, J.¹² Madison, V.¹³ Hammer, J.¹⁴ Sinigaglia, F.¹⁵ Steinmetz, M.¹⁶ Nagy, Z.A.¹⁷

27
- 0032493404
- Y. Tong Y. M. Fobian M. Wu N. D. Boyd K. D. Moeller Bioorg. Med. Chem. Lett. 1998 8 1679 l682
- (1998) Bioorg. Med. Chem. Lett. , vol.8
- Tong, Y.¹ Fobian, Y.M.² Wu, M.³ Boyd, N.D.⁴ Moeller, K.D.⁵

28
- 68049131110
- C. A. Thomas E. R. Talaty J. G. Bann Chem. Commun. 2009 3366 3368
- (2009) Chem. Commun. , pp. 3366-3368
- Thomas, C.A.¹ Talaty, E.R.² Bann, J.G.³

29
- 33845789244
- W. Kim K. I. Hardcastle V. P. Conticello Angew. Chem., Int. Ed. 2006 45 8141 8145
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 8141-8145
- Kim, W.¹ Hardcastle, K.I.² Conticello, V.P.³

30
- 13844320101
- C. M. Taylor R. Hardré P. J. B. Edwards J. Org. Chem. 2005 70 1306 1315
- (2005) J. Org. Chem. , vol.70 , pp. 1306-1315
- Taylor, C.M.¹ Hardré, R.² Edwards, P.J.B.³

31
- 0038514086
- C. L. Jenkins L. E. Bretscher I. A. Guzei R. T. Raines J. Am. Chem. Soc. 2003 125 6422 6427
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 6422-6427
- Jenkins, C.L.¹ Bretscher, L.E.² Guzei, I.A.³ Raines, R.T.⁴

32
- 38949165216
- L. Halab F. Gosselin W. D. Lubell Biopolymers (Pept. Sci.) 2000 55 101 122
- (2000) Biopolymers (Pept. Sci.) , vol.55 , pp. 101-122
- Halab, L.¹ Gosselin, F.² Lubell, W.D.³

33
- 0000617719
- E. Beausoleil R. Sharma S. W. Michnick W. D. Lubell J. Org. Chem. 1998 63 6572 6578
- (1998) J. Org. Chem. , vol.63 , pp. 6572-6578
- Beausoleil, E.¹ Sharma, R.² Michnick, S.W.³ Lubell, W.D.⁴

34
- 0021093584
- J. L. Flippen-Anderson R. Gilardi I. L. Karle M. H. Frey S. J. Opella L. M. Gierasch M. Goodman V. Madison N. G. Delaney J. Am. Chem. Soc. 1983 105 6609 6614
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 6609-6614
- Flippen-Anderson, J.L.¹ Gilardi, R.² Karle, I.L.³ Frey, M.H.⁴ Opella, S.J.⁵ Gierasch, L.M.⁶ Goodman, M.⁷ Madison, V.⁸ Delaney, N.G.⁹

35
- 0001490908
- N. G. Delaney V. Madison J. Am. Chem. Soc. 1982 104 6635 6641
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6635-6641
- Delaney, N.G.¹ Madison, V.²

36
- 79955057486
- K. Guitot M. Larregola T. K. Pradhan J.-L. Vasse S. Lavielle P. Bertus J. Szymoniak O. Lequin P. Karoyan ChemBioChem 2011 12 1039 1042
- (2011) ChemBioChem , vol.12 , pp. 1039-1042
- Guitot, K.¹ Larregola, M.² Pradhan, T.K.³ Vasse, J.-L.⁴ Lavielle, S.⁵ Bertus, P.⁶ Szymoniak, J.⁷ Lequin, O.⁸ Karoyan, P.⁹

37
- 75649147431
- C. Mothes M. Larregola J. Quancard N. Goasdoué S. Lavielle G. Chassaing O. Lequin P. Karoyan ChemBioChem 2010 11 55 58
- (2010) ChemBioChem , vol.11 , pp. 55-58
- Mothes, C.¹ Larregola, M.² Quancard, J.³ Goasdoué, N.⁴ Lavielle, S.⁵ Chassaing, G.⁶ Lequin, O.⁷ Karoyan, P.⁸

38
- 0346363687
- J. Quancard P. Karoyan O. Lequin E. Wenger A. Aubry S. Lavielle G. Chassaing Tetrahedron Lett. 2004 45 623 625
- (2004) Tetrahedron Lett. , vol.45 , pp. 623-625
- Quancard, J.¹ Karoyan, P.² Lequin, O.³ Wenger, E.⁴ Aubry, A.⁵ Lavielle, S.⁶ Chassaing, G.⁷

39
- 0030738499
- Torsion angles (,ψ) for an ideal βI-turn: in i+1 (-60,-30), in i+2 (-90,0); for an ideal βII-turn: in i+1 (-60,120), in i+2 (80,0). Note that they differ in the i+1 ψ and the i+2 angles, as a consequence of a ≈ 180° flip of the plane defined by the central amide group
- P. W. Baures W. H. Ojala W. B. Gleason R. L. Johnson J. Pept. Res. 1997 50 1 13
- (1997) J. Pept. Res. , vol.50 , pp. 1-13
- Baures, P.W.¹ Ojala, W.H.² Gleason, W.B.³ Johnson, R.L.⁴

40
- 0000559661
- A. Aubry M. T. Cung M. Marraud J. Am. Chem. Soc. 1985 107 7640 7647
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 7640-7647
- Aubry, A.¹ Cung, M.T.² Marraud, M.³

41
- 49549139072
- B. Castro J. R. Dormoy G. Evin C. Selve Tetrahedron Lett. 1975 14 1219 1222
- (1975) Tetrahedron Lett. , vol.14 , pp. 1219-1222
- Castro, B.¹ Dormoy, J.R.² Evin, G.³ Selve, C.⁴

42
- 4244099388
- R. Bardi A. M. Piazzesi C. Toniolo N. Sen H. Balaram P. Balaram Acta Crystallogr., Sect. C 1988 44 1972 1976
- (1988) Acta Crystallogr., Sect. C , vol.44 , pp. 1972-1976
- Bardi, R.¹ Piazzesi, A.M.² Toniolo, C.³ Sen, N.⁴ Balaram, H.⁵ Balaram, P.⁶

43
- 0037548464
- A. I. Jiménez C. Cativiela J. Gómez-Catalán J. J. Pérez A. Aubry M. París M. Marraud J. Am. Chem. Soc. 2000 122 5811 5821
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5811-5821
- Jiménez, A.I.¹ Cativiela, C.² Gómez-Catalán, J.³ Pérez, J.J.⁴ Aubry, A.⁵ París, M.⁶ Marraud, M.⁷

44
- 0032560953
- See the ESI
- A. I. Jiménez C. Cativiela A. Aubry M. Marraud J. Am. Chem. Soc. 1998 120 9452 9459
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 9452-9459
- Jiménez, A.I.¹ Cativiela, C.² Aubry, A.³ Marraud, M.⁴

45
- 33845379253
- R. O. Gould A. M. Gray P. Taylor M. D. Walkinshaw J. Am. Chem. Soc. 1985 107 5921 5927
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 5921-5927
- Gould, R.O.¹ Gray, A.M.² Taylor, P.³ Walkinshaw, M.D.⁴

46
- 0020787793
- E. Benedetti G. Morelli G. Némethy H. A. Scheraga Int. J. Pept. Protein Res. 1983 22 1 15
- (1983) Int. J. Pept. Protein Res. , vol.22 , pp. 1-15
- Benedetti, E.¹ Morelli, G.² Némethy, G.³ Scheraga, H.A.⁴

47
- 84985653863
- 1 rotamers (using the equation in ref. 16, as done in ref. 10) for the new J values are: 50% gauche(-) for d-Phe in 6; 56% gauche(+) for l-Phe in 5
- M. T. Cung M. Marraud Biopolymers 1982 21 953 967
- (1982) Biopolymers , vol.21 , pp. 953-967
- Cung, M.T.¹ Marraud, M.²

48
- 31944446531
- R. Mahalakshmi S. Raghothama P. Balaram J. Am. Chem. Soc. 2006 128 1125 1138
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1125-1138
- Mahalakshmi, R.¹ Raghothama, S.² Balaram, P.³

49
- 0242417008
- E. A. Meyer R. K. Castellano F. Diederich Angew. Chem., Int. Ed. 2003 42 1210 1250
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1210-1250
- Meyer, E.A.¹ Castellano, R.K.² Diederich, F.³

50
- 0025878347
- C. A. Hunter J. Singh J. M. Thornton J. Mol. Biol. 1991 218 837 846
- (1991) J. Mol. Biol. , vol.218 , pp. 837-846
- Hunter, C.A.¹ Singh, J.² Thornton, J.M.³

51
- 0024260626
- S. K. Burley G. A. Petsko Adv. Protein Chem. 1988 39 125 189
- (1988) Adv. Protein Chem. , vol.39 , pp. 125-189
- Burley, S.K.¹ Petsko, G.A.²

52
- 0022419375
- S. K. Burley G. A. Petsko Science 1985 229 23 28
- (1985) Science , vol.229 , pp. 23-28
- Burley, S.K.¹ Petsko, G.A.²

53
- 0001522355
- The γ and δ hydrogens of the pyrrolidine ring have been labelled as endo or exo depending on whether they are on the same or the opposite side of the ring as the carbonyl group, respectively
- T. Ashida M. Kakudo Bull. Chem. Soc. Jpn 1974 47 1129 1133
- (1974) Bull. Chem. Soc. Jpn , vol.47 , pp. 1129-1133
- Ashida, T.¹ Kakudo, M.²

54
- 20444483055
- The equation including the β-effect was used The Haasnoot-Altona equation from ref. 21 was used as implemented in the free-access program MestReJ
- C. A. G. Haasnoot F. A. A. M. de Leeuw C. Altona Tetrahedron 1980 36 2783 2792.
- (1980) Tetrahedron , vol.36 , pp. 2783-2792
- Haasnoot, C.A.G.¹ De Leeuw, F.A.A.M.² Altona, C.³

55
- 5444262691
- A. Navarro-Vázquez J. C. Cobas F. J. Sardina J. Casanueva E. Díez J. Chem. Inf. Comput. Sci. 2004 44 1680 1685
- (2004) J. Chem. Inf. Comput. Sci. , vol.44 , pp. 1680-1685
- Navarro-Vázquez, A.¹ Cobas, J.C.² Sardina, F.J.³ Casanueva, J.⁴ Díez, E.⁵

56
- 38149087413
- E. Aliev D. Courtier-Murias J. Phys. Chem. B 2007 111 14034 14042
- (2007) J. Phys. Chem. B , vol.111 , pp. 14034-14042
- Aliev, E.¹ Courtier-Murias, D.²

57
- 0038722138
- J. Quancard P. Karoyan S. Sagan O. Convert S. Lavielle G. Chassaing O. Lequin Eur. J. Biochem. 2003 270 2869 2878
- (2003) Eur. J. Biochem. , vol.270 , pp. 2869-2878
- Quancard, J.¹ Karoyan, P.² Sagan, S.³ Convert, O.⁴ Lavielle, S.⁵ Chassaing, G.⁶ Lequin, O.⁷

58
- 0003517973
- University of Göttingen: Göttingen
- G. M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen: Göttingen, 1997
- (1997) SHELXS-97, Program for the Solution of Crystal Structures
- Sheldrick, G.M.¹

59
- 0003495066
- University of Göttingen: Göttingen
- G. M. Sheldrick, SHELXL-97. Program for the Refinement of Crystal Structures, University of Göttingen: Göttingen, 1997
- (1997) SHELXL-97. Program for the Refinement of Crystal Structures
- Sheldrick, G.M.¹

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