SCOPUS 정보 검색 플랫폼

Volumn 64, Issue 20, 1999, Pages 7388-7394

Novel solid-phase synthesis of azapeptides and azapeptoides via Fmoc- strategy and its application in the synthesis of RGD-mimetics

(5) Gibson, Christoph a Goodman, Simon L b Hahn, Diane b Hölzemann, Günter b Kessler, Horst a

a TECHNICAL UNIVERSITY OF MUNICH (Germany)

b MERCK KGAA (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; ASPARTIC ACID; GLYCINE; PEPTIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIGAND BINDING; PEPTIDE SYNTHESIS; PROTEIN CONFORMATION; SOLID STATE;

EID: 0033214140 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo9906173 Document Type: Article

Times cited : (76)

References (52)

1
- 0028243847
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1994) J. Med. Chem. , vol.37 , pp. 1233-1251
- Gallop, M.A.¹ Barrett, R.W.² Dower, W.J.³ Fodor, S.P.A.⁴ Gordon, E.M.⁵

2
- 0029065615
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1995) Tetrahedron , vol.51 , pp. 8135-8173
- Terrett, N.K.¹ Gardner, M.² Gordon, D.W.³ Kobylecki, R.J.⁴ Steele, J.⁵

3
- 0032542115
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2289-2337
- Balkenhohl, F.¹ Bussche-Hünnefeld, C.V.D.² Lansky, A.³ Zechel, C.⁴

4
- 0032542115
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1996) Contemp. Org. Synth. , pp. 216-237
- Brown, R.¹

5
- 7044263277
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1996) Chem. Rev. , vol.96 , pp. 555-600
- Thompson, L.A.¹ Ellman, J.A.²

6
- 33749100952
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3293-3320
- Brown, R.C.D.¹

7
- 0001732712
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1998) Synlett , pp. 817-830
- Brown, A.R.¹ Hermkens, P.H.H.² Ottenheijm, H.C.J.³ Rees, D.C.⁴

8
- 0032087776
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 386-396
- Whittaker, M.¹

9
- 0029930278
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1996) Tetrahedron , vol.52 , pp. 4527-4554
- Hermkens, P.H.H.¹ Ottenheijm, H.C.J.² Rees, D.³

10
- 0031001699
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643-5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1997) Tetrahedron , vol.63 , pp. 5643-5678
- Hermkens, P.H.H.¹ Ottenheijm, H.C.J.² Rees, D.C.³

11
- 0032542115
- For reviews of solid-phase synthesis, see: (a) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135-8173. (c) Balkenhohl, F.; Bussche-Hünnefeld, C. v. d.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2289-2337. (d) Brown, R. Contemp. Org. Synth. 1996, 216-237. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 817-830. (h) Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396. For listings of solid-phase reactions, see: (i) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554. (j) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 63, 5643- 5678. (k) Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385-15443.
- (1998) Tetrahedron , vol.54 , pp. 15385-15443
- Booth, S.¹ Hermkens, P.H.H.² Ottenheijm, H.C.J.³ Rees, D.C.⁴

12
- 0028038601
- For reviews, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720. (b) Giannis, A.; Rübsam, F. Adv. Drug Res. 1997, 29, 1-78. (c) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441-52.
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1699-1720
- Gante, J.¹

13
- 0030845948
- For reviews, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720. (b) Giannis, A.; Rübsam, F. Adv. Drug Res. 1997, 29, 1-78. (c) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441-52.
- (1997) Adv. Drug Res. , vol.29 , pp. 1-78
- Giannis, A.¹ Rübsam, F.²

14
- 0032133429
- For reviews, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720. (b) Giannis, A.; Rübsam, F. Adv. Drug Res. 1997, 29, 1-78. (c) Ripka, A. S.; Rich, D. H. Curr. Opin. Chem. Biol. 1998, 2, 441-52.
- (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 441-452
- Ripka, A.S.¹ Rich, D.H.²

15
- 0000908874
- The term peptoid is used as proposed by Zuckermann et al. J. Am. Chem. Soc. 1992, 114, 10646-10647.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10646-10647
- Zuckermann¹

16
- 0344799568
- Doctoral thesis, Munich, 1996. Schmitt, J. Doctoral thesis, Munich
- Wermuth, J. Doctoral thesis, Munich, 1996. Schmitt, J. Doctoral thesis, Munich, 1998.
- (1998)
- Wermuth, J.¹

17
- 0030768536
- For recent reviews, see: (a) Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1374-1389. (b) Samanen, J.; Jonak, Z.; Rieman, D.; Yue, T.-L. Curr. Pharm. Des. 1997, 3, 545- 584.
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1374-1389
- Haubner, R.¹ Finsinger, D.² Kessler, H.³

18
- 0030782039
- For recent reviews, see: (a) Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1374-1389. (b) Samanen, J.; Jonak, Z.; Rieman, D.; Yue, T.-L. Curr. Pharm. Des. 1997, 3, 545-584.
- (1997) Curr. Pharm. Des. , vol.3 , pp. 545-584
- Samanen, J.¹ Jonak, Z.² Rieman, D.³ Yue, T.-L.⁴

19
- 0345230500
- JAI Press Inc.: London
- For reviews, see: (a) Barker, P. L.; Webb, R. R. Antiplatelet and antithrombotic agents: From viper venom proteins, to peptides and peptidomimetics to small organic molecules; JAI Press Inc.: London, 1995; Vol. 3. (b) Ojima, I.; Chakravarty, S.; Dong, Q. Bioorg. Med. Chem. 1995, 3, 337-360.
- (1995) Antiplatelet and Antithrombotic Agents: From Viper Venom Proteins, to Peptides and Peptidomimetics to Small Organic Molecules , vol.3
- Barker, P.L.¹ Webb, R.R.²

20
- 0029055340
- For reviews, see: (a) Barker, P. L.; Webb, R. R. Antiplatelet and antithrombotic agents: From viper venom proteins, to peptides and peptidomimetics to small organic molecules; JAI Press Inc.: London, 1995; Vol. 3. (b) Ojima, I.; Chakravarty, S.; Dong, Q. Bioorg. Med. Chem. 1995, 3, 337-360.
- (1995) Bioorg. Med. Chem. , vol.3 , pp. 337-360
- Ojima, I.¹ Chakravarty, S.² Dong, Q.³

21
- 0031965374
- Goligorsky, M. S.; Kessler, H.; Romanov, V. I. Nephrol. Dial. Transplant. 1998, 13, 254-263.
- (1998) Nephrol. Dial. Transplant. , vol.13 , pp. 254-263
- Goligorsky, M.S.¹ Kessler, H.² Romanov, V.I.³

22
- 0029902950
- and references therein
- Reynolds, C. H.; Hormann, R. E. J. Am. Chem. Soc. 1996, 118, 9395-9401 and references therein.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9395-9401
- Reynolds, C.H.¹ Hormann, R.E.²

23
- 85082699866
- For review of solution phase syntheses of azapeptide, see: Gante, J. Synthesis 1989, 405-413.
- (1989) Synthesis , pp. 405-413
- Gante, J.¹

24
- 0029988589
- Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539-2544.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2539-2544
- Han, H.¹ Janda, K.D.²

25
- 37049076684
- Quibell, M.; Turnell, W. G.; Johnson, T. J. Chem. Soc., Perkin Trans. 1 1993, 2843-2849.
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 2843-2849
- Quibell, M.¹ Turnell, W.G.² Johnson, T.³

26
- 0031263756
- (a) André, F.; Marraud, M.; Tsouloufis, T.; Tzartos, S. J.; Boussard, G. J. Peptide Sci. 1997, 3, 429-441.
- (1997) J. Peptide Sci. , vol.3 , pp. 429-441
- André, F.¹ Marraud, M.² Tsouloufis, T.³ Tzartos, S.J.⁴ Boussard, G.⁵

27
- 0003543901
- (b) Frochot, C.; Vandersesse, R.; Driou, A.; Linden, G.; Marraud, M.; Cung, M. T. Lett. Pept. Sci. 1997, 4, 219-225.
- (1997) Lett. Pept. Sci. , vol.4 , pp. 219-225
- Frochot, C.¹ Vandersesse, R.² Driou, A.³ Linden, G.⁴ Marraud, M.⁵ Cung, M.T.⁶

28
- 20744456789
- (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
- Merrifield, R.B.¹

29
- 0025232814
- For comprehensive reviews on SPPS, see: (b) Fields, G. B.; Noble, R. L. Int. J. Pept. Protein Res. 1990, 35, 161-214.
- (1990) Int. J. Pept. Protein Res. , vol.35 , pp. 161-214
- Fields, G.B.¹ Noble, R.L.²

30
- 0003423120
- Academic Press: New York
- Solid-Phase Peptide Synthesis in Methods in Enzymology; Fields, G. B., Ed.; Academic Press: New York, 1997; Vol. 289.
- (1997) Solid-Phase Peptide Synthesis in Methods in Enzymology , vol.289
- Fields, G.B.¹

31
- 33947091567
- For the preparation of Fmoc-hydrazine, see: Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404-3409.
- (1972) J. Org. Chem. , vol.37 , pp. 3404-3409
- Carpino, L.A.¹ Han, G.Y.²

32
- 0001005576
- Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929-3934.
- (1996) J. Org. Chem. , vol.61 , pp. 3929-3934
- Nowick, J.S.¹ Holmes, D.L.² Noronha, G.³ Smith, E.M.⁴ Nguyen, T.M.⁵ Huang, S.-L.⁶

33
- 0030067674
- (a) André, F.; Marraud, M.; Boussard, G. Tetrahedron Lett. 1996, 37, 183-186.
- (1996) Tetrahedron Lett. , vol.37 , pp. 183-186
- André, F.¹ Marraud, M.² Boussard, G.³

34
- 0030773550
- (b) André, F.; Vicherat, A.; Boussard, G.; Aubry, A.; Marraud, M. J. Peptide Res. 1987, 50, 372-381.
- (1987) J. Peptide Res. , vol.50 , pp. 372-381
- André, F.¹ Vicherat, A.² Boussard, G.³ Aubry, A.⁴ Marraud, M.⁵

35
- 0001216513
- Holmes, C. P.; Jones, D. G. J. Org. Chem. 1995, 60, 2318-2319.
- (1995) J. Org. Chem. , vol.60 , pp. 2318-2319
- Holmes, C.P.¹ Jones, D.G.²

36
- 0026419328
- (a) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
- (1991) Nature , vol.354 , pp. 82-84
- Lam, K.S.¹ Salmon, S.E.² Hersh, E.M.³ Hruby, V.J.⁴ Kazmierski, W.M.⁵ Knapp, R.J.⁶

37
- 0000577984
- (b) Lam, K. S.; Lebl, M.; Krchnák, V. Chem. Rev. 1997, 97, 411-448.
- (1997) Chem. Rev. , vol.97 , pp. 411-448
- Lam, K.S.¹ Lebl, M.² Krchnák, V.³

38
- 0006163330
- (a) Stempel, A.; Zelauskas, J.; Aeschlimann, J. A. J. Org. Chem. 1955, 20, 412-418.
- (1955) J. Org. Chem. , vol.20 , pp. 412-418
- Stempel, A.¹ Zelauskas, J.² Aeschlimann, J.A.³

39
- 0345662510
- (b) Gante, J. Chem. Ber. 1965, 98, 530-547.
- (1965) Chem. Ber. , vol.98 , pp. 530-547
- Gante, J.¹

40
- 0026656122
- Frank, R. Tetrahedron 1992, 48, 9217-9232.
- (1992) Tetrahedron , vol.48 , pp. 9217-9232
- Frank, R.¹

41
- 0026108692
- Fodor, S. P. A.; Read, J. L.; Pirrung, M. C.; Stryer, L.; Lu, A. T.; Solas, D. Science 1991, 251, 767-773.
- (1991) Science , vol.251 , pp. 767-773
- Fodor, S.P.A.¹ Read, J.L.² Pirrung, M.C.³ Stryer, L.⁴ Lu, A.T.⁵ Solas, D.⁶

42
- 33751386272
- Vedejs, E.; Bennett, N. S.; Conn, L. m.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286-7288.
- (1993) J. Org. Chem. , vol.58 , pp. 7286-7288
- Vedejs, E.¹ Bennett, N.S.² Conn, L.M.³ Diver, S.T.⁴ Gingras, M.⁵ Lin, S.⁶ Oliver, P.A.⁷ Peterson, M.J.⁸

43
- 0006232924
- (a) Wu, Y.; Matsueda, G. R.; Bernatowicz, M. Synth. Commun. 1993, 23, 2055-3060.
- (1993) Synth. Commun. , vol.23 , pp. 2055-3060
- Wu, Y.¹ Matsueda, G.R.² Bernatowicz, M.³

44
- 0030948518
- For a comparison of different guanylating agents in SPS, see: (b) Robinson, S.; Roskamp, E. Tetrahedron 1987, 53, 6697-6705.
- (1987) Tetrahedron , vol.53 , pp. 6697-6705
- Robinson, S.¹ Roskamp, E.²

45
- 0025880146
- (a) Aumailley, M.; Gurrath, M.; Müller, G.; Calvete, J.; Timpl, R.; Kessler, H. FEBS Lett. 1991, 291, 50-54.
- (1991) FEBS Lett. , vol.291 , pp. 50-54
- Aumailley, M.¹ Gurrath, M.² Müller, G.³ Calvete, J.⁴ Timpl, R.⁵ Kessler, H.⁶

46
- 0027997413
- (b) Pfaff, M.; Tangemann, B.; Müller, B.; Gurrath, M.; Müller, G.; Kessler, H.; Timpl, R.; Engel, J. J. Biol. Chem. 1994, 269, 20233-20238.
- (1994) J. Biol. Chem. , vol.269 , pp. 20233-20238
- Pfaff, M.¹ Tangemann, B.² Müller, B.³ Gurrath, M.⁴ Müller, G.⁵ Kessler, H.⁶ Timpl, R.⁷ Engel, J.⁸

47
- 0344799550
- note
- The pair of singlets results from two conformers as shown in the HMQC-COSY and HMBC, respectively.

48
- 0028984231
- Mitjans, F.; Sander, D.; Adan, J.; Sutter, A.; Martinez, J. M.; Jaggle, C. S.; Moyano, J. M.; Kreysch, H. G.; Piulats, J.; Goodman, S. L. J. Cell Sci. 1995, 108, 2825-2838.
- (1995) J. Cell Sci. , vol.108 , pp. 2825-2838
- Mitjans, F.¹ Sander, D.² Adan, J.³ Sutter, A.⁴ Martinez, J.M.⁵ Jaggle, C.S.⁶ Moyano, J.M.⁷ Kreysch, H.G.⁸ Piulats, J.⁹ Goodman, S.L.¹⁰

49
- 0022502048
- Pytela, R.; Pierschbacher, M. D.; Ginsberg, M. H.; Plow, E. F.; Ruoslahti, E. Science 1986, 231, 1559-1562.
- (1986) Science , vol.231 , pp. 1559-1562
- Pytela, R.¹ Pierschbacher, M.D.² Ginsberg, M.H.³ Plow, E.F.⁴ Ruoslahti, E.⁵

50
- 0024230916
- (a) Smith, J. W.; Cheresh, D. A. J. Biol. Chem. 1988, 263, 18726-18731.
- (1988) J. Biol. Chem. , vol.263 , pp. 18726-18731
- Smith, J.W.¹ Cheresh, D.A.²

51
- 0025340173
- (b) Smith, J. W.; Vestal, D. J.; Irwin, S. V.; Burke, T. A.; Cheresh, D. A. J. Biol. Chem. 1990, 265, 11008-11013.
- (1990) J. Biol. Chem. , vol.265 , pp. 11008-11013
- Smith, J.W.¹ Vestal, D.J.² Irwin, S.V.³ Burke, T.A.⁴ Cheresh, D.A.⁵

52
- 0029789066
- Haubner, R; Schmitt, W.; Hölzemann, G.; Goodman, S. L.; Jonczyk, A.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881-7891.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7881-7891
- Haubner, R.¹ Schmitt, W.² Hölzemann, G.³ Goodman, S.L.⁴ Jonczyk, A.⁵ Kessler, H.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.