메뉴 건너뛰기




Volumn 121, Issue 9, 1999, Pages 1806-1816

β-turn and β-hairpin mimicry with tetrasubstituted alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DICHLOROMETHANE; PEPTIDE DERIVATIVE;

EID: 0033541110     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9824526     Document Type: Article
Times cited : (91)

References (82)
  • 1
    • 0025409471 scopus 로고
    • For leading references, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55. (b) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 12, 1244. (c) Gillespie, P.; Cicariello, J.; Olsen, G. L. Biopolymers 1997, 43, 191. (d) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
    • (1990) J. Mol. Recog. , vol.3 , pp. 55
    • Ball, J.B.1    Alewood, P.F.2
  • 2
    • 33745502124 scopus 로고
    • For leading references, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55. (b) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 12, 1244. (c) Gillespie, P.; Cicariello, J.; Olsen, G. L. Biopolymers 1997, 43, 191. (d) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.12 , pp. 1244
    • Giannis, A.1    Kolter, T.2
  • 3
    • 0030964528 scopus 로고    scopus 로고
    • For leading references, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55. (b) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 12, 1244. (c) Gillespie, P.; Cicariello, J.; Olsen, G. L. Biopolymers 1997, 43, 191. (d) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
    • (1997) Biopolymers , vol.43 , pp. 191
    • Gillespie, P.1    Cicariello, J.2    Olsen, G.L.3
  • 4
    • 0030768259 scopus 로고    scopus 로고
    • For leading references, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55. (b) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 12, 1244. (c) Gillespie, P.; Cicariello, J.; Olsen, G. L. Biopolymers 1997, 43, 191. (d) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
    • (1997) Tetrahedron , vol.53 , pp. 12789
    • Hanessian, S.1    McNaughton-Smith, G.2    Lombart, H.-G.3    Lubell, W.D.4
  • 5
    • 0029949745 scopus 로고    scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4249
    • Kemp, D.S.1    Oslick, S.L.2    Allen, T.J.3
  • 6
    • 0025079448 scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1990) J. Org. Chem. , vol.55 , pp. 4650
    • Kemp, D.S.1    Bowen, B.R.2    Muendel, C.C.3
  • 7
    • 0028348938 scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 70
    • Brandmeier, V.1    Sauer, W.H.B.2    Feigel, M.3
  • 8
    • 0030037714 scopus 로고    scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 5836
    • Nesloney, C.L.1    Kelly, J.W.2
  • 9
    • 0030702048 scopus 로고    scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10903
    • Nowick, J.S.1    Iasaf, S.2
  • 10
    • 0030824028 scopus 로고    scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1745
    • Schopfer, U.1    Stahl, M.2    Brandl, T.3    Hoffmann, R.W.4
  • 11
    • 0000478078 scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1995) Chem. Rev. , vol.95 , pp. 2169
    • Schneider, J.P.1    Kelly, J.W.2
  • 12
    • 0000847536 scopus 로고    scopus 로고
    • For leading references, see: (a) Kemp, D. S.; Oslick, S. L.; Allen, T. J. J. Am. Chem. Soc. 1996, 118, 4249. (b) Kemp, D. S.; Bowen, B. R.; Muendel, C. C. J. Org. Chem. 1990, 55, 4650. (c) Brandmeier, V.; Sauer, W. H. B.; Feigel, M. Helv. Chim. Acta 1994, 77, 70. (d) Nesloney, C. L.; Kelly, J. W. J. Am. Chem. Soc. 1996, 118, 5836. (e) Nowick, J. S.; Iasaf, S. J. Am. Chem. Soc. 1997, 119, 10903. (f) Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745. (g) Schneider, J. P.; Kelly, J. W. Chem. Rev. 1995, 95, 2169. (h) Nowick, J. S.; Smith, E. M.; Pairish, M. Chem. Soc. Rev. 1996, 401.
    • (1996) Chem. Soc. Rev. , pp. 401
    • Nowick, J.S.1    Smith, E.M.2    Pairish, M.3
  • 19
    • 33748542524 scopus 로고
    • General discussions of allylic strain: Johnson, F. Chem. Rev. 1968, 68, 375. Berg, U.; Sandström, J. Adv. Phys. Org. Chem. 1989, 25, 1. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124. For the use of acyclic stereochemical control to preorganize the backbone of a saturated alkane hairpin mimic, see: Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745.
    • (1968) Chem. Rev. , vol.68 , pp. 375
    • Johnson, F.1
  • 20
    • 0343262105 scopus 로고
    • General discussions of allylic strain: Johnson, F. Chem. Rev. 1968, 68, 375. Berg, U.; Sandström, J. Adv. Phys. Org. Chem. 1989, 25, 1. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124. For the use of acyclic stereochemical control to preorganize the backbone of a saturated alkane hairpin mimic, see: Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745.
    • (1989) Adv. Phys. Org. Chem. , vol.25 , pp. 1
    • Berg, U.1    Sandström, J.2
  • 21
    • 0026640040 scopus 로고
    • General discussions of allylic strain: Johnson, F. Chem. Rev. 1968, 68, 375. Berg, U.; Sandström, J. Adv. Phys. Org. Chem. 1989, 25, 1. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124. For the use of acyclic stereochemical control to preorganize the backbone of a saturated alkane hairpin mimic, see: Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1124
    • Hoffmann, R.W.1
  • 22
    • 0030824028 scopus 로고    scopus 로고
    • General discussions of allylic strain: Johnson, F. Chem. Rev. 1968, 68, 375. Berg, U.; Sandström, J. Adv. Phys. Org. Chem. 1989, 25, 1. Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1992, 31, 1124. For the use of acyclic stereochemical control to preorganize the backbone of a saturated alkane hairpin mimic, see: Schopfer, U.; Stahl, M.; Brandl, T.; Hoffmann, R. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 1745.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1745
    • Schopfer, U.1    Stahl, M.2    Brandl, T.3    Hoffmann, R.W.4
  • 30
    • 0000291574 scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4105
    • Haque, T.S.1    Little, J.C.2    Gellman, S.H.3
  • 31
    • 0029931671 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 6975
    • Haque, T.S.1    Little, J.C.2    Gellman, S.H.3
  • 32
    • 0030992473 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2303
    • Haque, T.S.1    Gellman, S.H.2
  • 33
    • 0001561813 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4236
    • Stanger, H.E.1    Gellman, S.H.2
  • 34
    • 0040614570 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1997) J. Am. Chem. Soc. , vol.120 , pp. 44869
    • Schenck, H.L.1    Gellman, S.H.2
  • 35
    • 0028972051 scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1995) Biochem. Biophys. Res. Commun. , vol.216 , pp. 375
    • Awasthi, S.K.1    Raghothama, S.2    Balaram, P.3
  • 36
    • 0029758829 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 8189
    • Karle, I.L.1    Awasthi, S.K.2    Balaram, P.3
  • 37
    • 0346837918 scopus 로고    scopus 로고
    • Use of D-Pro-Xxx segments to promote β-hairpin formation: (a) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105. (b) Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975. (c) Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1997, 119, 2303. (d) Stanger, H. E.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 4236. (e) Schenck, H. L.; Gellman, S. H. J. Am. Chem. Soc. 1997, 120, 44869. (f) Awasthi, S. K.; Raghothama, S.; Balaram, P. Biochem. Biophys. Res. Commun. 1995, 216, 375. (g) Karle, I. L.; Awasthi, S. K.; Balaram, P. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8189. (h) Ragothama, S. R.; Awasthi, S. K.; Balaram, P. J. Chem. Soc., Perkin Trans. 2 1998, 137.
    • (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 137
    • Ragothama, S.R.1    Awasthi, S.K.2    Balaram, P.3
  • 38
    • 0029891313 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1996) Nature Struct. Biol. , vol.3 , pp. 604
    • Ramírez-Alvarado, M.1    Blanco, F.J.2    Serrano, L.3
  • 39
    • 1842403587 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 175
    • De Alba, E.1    Jimenez, M.A.2    Rico, M.3
  • 40
    • 0030752929 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 1297
    • Maynard, A.J.1    Searle, M.S.2
  • 41
    • 1542579435 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 1955
    • Sharman, G.J.1    Searle, M.S.2
  • 42
    • 21844448091 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 789
    • Griffiths-Jones, S.R.1    Maynard, A.J.2    Sharman, G.J.3    Searle, M.S.4
  • 43
    • 0032507251 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1996
    • Maynard, A.J.1    Sharman, G.J.2    Searle, M.S.3
  • 44
    • 0032479010 scopus 로고    scopus 로고
    • Use of the L-Asn-Gly segment to promote β-hairpin formation: (i) Ramírez-Alvarado, M.; Blanco, F. J.; Serrano, L. Nature Struct. Biol. 1996, 3, 604. (j) de Alba, E.; Jimenez, M. A.; Rico, M. J. Am. Chem. Soc. 1997, 119, 175. (k) Maynard, A. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1297. (l) Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1997, 1955. (m) Griffiths-Jones, S. R.; Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Chem. Soc., Chem. Commun. 1998, 789. (n) Maynard, A. J.; Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 1996. (o) Sharman, G. J.; Searle, M. S. J. Am. Chem. Soc. 1998, 120, 5291.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5291
    • Sharman, G.J.1    Searle, M.S.2
  • 45
    • 0345218925 scopus 로고    scopus 로고
    • note
    • (p) We have recently shown that D-Pro-Gly is a stronger hairpin promoter than L-Asn-Gly (ref 9d).
  • 49
    • 0000810926 scopus 로고    scopus 로고
    • and references therein
    • (c) Varani, G. Acc. Chem. Res. 1997, 30, 189 and references therein.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 189
    • Varani, G.1
  • 50
    • 0015101706 scopus 로고
    • 3 bonds: Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678. Expansion of this concept: Mammen, M.; Shakhnovich, E. I.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3168.
    • (1971) Proc. Natl. Acad. Sci. U.S.A. , vol.68 , pp. 1678
    • Page, M.I.1    Jencks, W.P.2
  • 51
    • 0000598486 scopus 로고    scopus 로고
    • 3 bonds: Page, M. I.; Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1678. Expansion of this concept: Mammen, M.; Shakhnovich, E. I.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3168.
    • (1998) J. Org. Chem. , vol.63 , pp. 3168
    • Mammen, M.1    Shakhnovich, E.I.2    Whitesides, G.M.3
  • 52
    • 0000368024 scopus 로고
    • We have previously shown that tri- and tetrasubstituted trans-alkene units provide greater backbone preorganization than a disubstituted trans-alkene unit, as manifested in intramolecular hydrogen bond formation: (a) Liang, G.-B.; Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1991, 113, 3994.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 3994
    • Liang, G.-B.1    Dado, G.P.2    Gellman, S.H.3
  • 54
    • 0040614566 scopus 로고
    • Computational prediction that a trans-trisubstituted alkene-based amide isostere will more strongly induce chain folding than a trans-disubstituted alkene: Deschrijver, P.; Tourwé, D. FEBS Lett. 1982, 146, 353. Recent experimental efforts to verify this prediction were unsuccessful: Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703.
    • (1982) FEBS Lett. , vol.146 , pp. 353
    • Deschrijver, P.1    Tourwé, D.2
  • 55
    • 0030034074 scopus 로고    scopus 로고
    • Computational prediction that a trans-trisubstituted alkene-based amide isostere will more strongly induce chain folding than a trans- disubstituted alkene: Deschrijver, P.; Tourwé, D. FEBS Lett. 1982, 146, 353. Recent experimental efforts to verify this prediction were unsuccessful: Devadder, S.; Verheyden, P.; Jaspers, H. C. M.; Van Binst, G.; Tourwé, D. Tetrahedron Lett. 1996, 37, 703.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 703
    • Devadder, S.1    Verheyden, P.2    Jaspers, H.C.M.3    Van Binst, G.4    Tourwé, D.5
  • 61
    • 0345650720 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Wisconsin-Madison
    • Gardner, R. R., Ph.D. Thesis, University of Wisconsin-Madison, 1997.
    • (1997)
    • Gardner, R.R.1
  • 71
    • 0344356247 scopus 로고    scopus 로고
    • Ref. 13b
    • (b) Ref. 13b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.