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1
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(a) For a recent review, see: Siligardi, G.; Drake, A. F. Peptide Sci. 1995, 37, 281. (b) For recent examples of proteins which bind PPII helices, see: Feng, S.; Chen, J. K.; Yu, H.; Simon, J. A.; Schreiber, S. L. Science 1994, 266, 1241. (c) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (d) Gorina, S.; Pavletich, N. P. Science 1996, 274, 1001. (e) Raj, P. A.; Marcus, E.; Edgerton, M. Biochemistry 1996, 35, 4314. (f) Lee, C.-H.; Saksela, K.; Mirza, U. A.; Chait, B. T.; Kuriyan, J. Cell 1996, 85, 931. (g) Feng, S.; Kasahara, C.; Rickles, R. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12408. (h) Jardetzky, T. S.; Brown, J. H.; Gorga, J. C.; Stern, L. J.; Urban, R. G.; Strominger, J. L.; Wiley, D. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 734. (i) Zeile, W. L.; Purich, D. L.; Southwick, F. S. J. Cell Biol. 1996, 133, 49.
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(a) For a recent review, see: Siligardi, G.; Drake, A. F. Peptide Sci. 1995, 37, 281. (b) For recent examples of proteins which bind PPII helices, see: Feng, S.; Chen, J. K.; Yu, H.; Simon, J. A.; Schreiber, S. L. Science 1994, 266, 1241. (c) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (d) Gorina, S.; Pavletich, N. P. Science 1996, 274, 1001. (e) Raj, P. A.; Marcus, E.; Edgerton, M. Biochemistry 1996, 35, 4314. (f) Lee, C.-H.; Saksela, K.; Mirza, U. A.; Chait, B. T.; Kuriyan, J. Cell 1996, 85, 931. (g) Feng, S.; Kasahara, C.; Rickles, R. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12408. (h) Jardetzky, T. S.; Brown, J. H.; Gorga, J. C.; Stern, L. J.; Urban, R. G.; Strominger, J. L.; Wiley, D. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 734. (i) Zeile, W. L.; Purich, D. L.; Southwick, F. S. J. Cell Biol. 1996, 133, 49.
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(a) For a recent review, see: Siligardi, G.; Drake, A. F. Peptide Sci. 1995, 37, 281. (b) For recent examples of proteins which bind PPII helices, see: Feng, S.; Chen, J. K.; Yu, H.; Simon, J. A.; Schreiber, S. L. Science 1994, 266, 1241. (c) Yu, H.; Chen, J. K.; Feng, S.; Dalgarno, D. C.; Brauer, A. W.; Schreiber, S. L. Cell 1994, 76, 933. (d) Gorina, S.; Pavletich, N. P. Science 1996, 274, 1001. (e) Raj, P. A.; Marcus, E.; Edgerton, M. Biochemistry 1996, 35, 4314. (f) Lee, C.-H.; Saksela, K.; Mirza, U. A.; Chait, B. T.; Kuriyan, J. Cell 1996, 85, 931. (g) Feng, S.; Kasahara, C.; Rickles, R. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12408. (h) Jardetzky, T. S.; Brown, J. H.; Gorga, J. C.; Stern, L. J.; Urban, R. G.; Strominger, J. L.; Wiley, D. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 734. (i) Zeile, W. L.; Purich, D. L.; Southwick, F. S. J. Cell Biol. 1996, 133, 49.
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2642645014
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note
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3N; however, this transformation remains unoptimized.
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2642681236
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note
-
For the PPII mimics 11 and 12, the NOEs between the N-terminal α-Hs and the cis and trans δ-Hs (cis and trans are assigned relative to the proline carbonyl) are of unequal intensity with the NOE between the trans δ-H and the α-H being more pronounced. Furthermore, the NOE between the tert-butyl group and the N-terminal trans δ-H is also greater than between the tert-butyl group and the N-terminal cis δ-H. Although pyrrolidine ring conformations are difficult to assign due to the small energy differences between conformers and the low energy of activation for five-member ring conformational interconversion, these observed NOEs can be tentatively assigned to a populated Cγ exo pyrrolidine ring conformation. The Cγ exo pucker thus places the trans δ-H into closer spacial relationship to the α-H of an N-terminally positioned PTAA (or to the tert-butyl group in the N-terminal residue). (Equation Presented)
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23
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