Identification of sequence selective receptors for peptides with a carboxylic acid terminus

Chemistry - A European Journal

Volumn 7, Issue 9, 2001, Pages 1889-1898

  Braxmeier, Tobias ^a   Demarcus, Mariangela ^a   Fessmann, Thilo ^a   McAteer, Stephen ^a   Kilburn, Jeremy D ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Combinatorial chemistry; Peptides; Receptors; Tweezers

Indexed keywords

DYES; RESINS; SCREENING;

DYE-LABEL;

CARBOXYLIC ACIDS;

CARBOXYLIC ACID; DIAMINOPYRIDINE; DYE; PEPTIDE; PEPTIDE LIBRARY; PYRIDINE DERIVATIVE; RECEPTOR; TRIPEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL BINDING; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; ENZYME SPECIFICITY; METABOLISM; MOLECULAR MIMICRY; PROTEIN BINDING; PROTEIN INTERACTION; SYNTHESIS;

AMINO ACID SEQUENCE; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; MOLECULAR MIMICRY; PEPTIDE LIBRARY; PEPTIDES; PROTEIN BINDING; RECEPTORS, PEPTIDE; SUBSTRATE SPECIFICITY;

EID: 0035805285     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010504)7:9<1889::AID-CHEM1889>3.0.CO;2-7     Document Type: Article

References (51)

1. For original work on tweezer receptors, see: a) C.-W. Chen, H. W. Whitlock Jr., J. Am. Chem. Soc. 1978, 100, 4921-4922; b) S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201.
2. For original work on tweezer receptors, see: a) C.-W. Chen, H. W. Whitlock Jr., J. Am. Chem. Soc. 1978, 100, 4921-4922; b) S. C. Zimmerman, W. Wu, Z. Zeng, J. Am. Chem. Soc. 1991, 113, 196-201.
3. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
4. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
5. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
6. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
7. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
8. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
9. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
10. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
11. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
12. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
13. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
14. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
15. For a recent review on peptide receptors see: M. W. Peczuh, A. D. Hamilton, Chem. Rev. 2000, 100, 2479-2493; other recent examples of sequence selective peptide receptors. see: a) P. D. Henley, C. P. Waymark, I. Gillies, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2000, 1021-1031; b) P. D. Henley, J. D. Kilburn, Chem. Commun. 1999, 1335-1336; c) R. Xu, G. Greiveldinger, L. E. Marenus, A. Cooper, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 4898-4899; d) M. Sirish, H.-J. Schneider, Chem. Commun. 1999, 907-908; e) H. Hioki, T. Yamada, C. Fujioka, M. Kodama, Tetrahedron Lett. 1999, 40, 6821-6825; f) J. Dowden, P. D. Edwards, S. S. Flack, J. D. Kilburn, Chem. Eur J. 1999, 5, 79-89; g) Md. A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11 208-11 209; h) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; i) W. C. Still, Acc. Chem. Res. 1996, 29, 155-163: j) B. Hinzen, P. Seiler, F. Diederich, Helv. Chim. Acta 1996, 79, 942-960; k) G. Jung, H. Hofstetter, S. Feiertag, D. Stoll, O. Hofstetter, K.-H. Wiesmüller, V. Schurig, Angew. Chem. 1996, 108, 2261-2263; Angew. Chem. Int. Ed. Engl. 1996, 35, 2148-2150 and references therein.
16. a) D. W. P. M. Löwik, M, D. Weingarten, M. Brockema, A. J. Brouwer, W. C. Still, R. M. J. Liskamp, Angew. Chem. 1998, 110, 1947-1950; Angew. Chem. Int. Ed. 1998, 37, 1846-1850;
17. a) D. W. P. M. Löwik, M, D. Weingarten, M. Brockema, A. J. Brouwer, W. C. Still, R. M. J. Liskamp, Angew. Chem. 1998, 110, 1947-1950; Angew. Chem. Int. Ed. 1998, 37, 1846-1850;
18. b) D. P. W. M. Löwik, S. J. E. Mulders, Y. Cheng, Y. Shao, R. M. J. Liskamp. Tetrahedron Lett. 1996, 37, 8253-8256;
19. c) C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765;
20. c) C. Gennari, H. P. Nestler, B. Salom, W. C. Still, Angew. Chem. 1995, 107, 1894-1896; Angew. Chem. Int. Ed. Engl. 1995, 34, 1765;
21. d) H. Wennemers, S. S. Yoon, W. C. Still, J. Org. Chem. 1995, 60, 1108-1109.
22. a) M. Davies, M. Bonnat, F. Guillier, J. D. Kilburn, M. Bradley, J. Org. Chem. 1998, 63, 8696-8703;
23. b) M. Torneiro, W. C. Still. Tetrahedron, 1997, 53, 8739-8750;
24. c) S. R. LaBrenz, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 1655-1656.
25. a) Y. Cheng, T. Suenaga, W. C. Still, J. Am. Chem. Soc. 1996, 118, 1813-1814;
26. b) R. Boyce, G. Li, H. P. Nestler, T. Suenaga, W. C. Still. J. Am. Chem. Soc. 1994, 116, 7955-7956;
27. c) H. P. Nestler, Molecular Diversity 1996, 2, 35-40. See also refs. [2c, e, i].
28. T. Fessmann, J. D. Kilburn, Angew. Chem. 1999, 111, 2170-2174; Angew. Chem. Int. Ed. 1999, 38, 1993-1996.
29. T. Fessmann, J. D. Kilburn, Angew. Chem. 1999, 111, 2170-2174; Angew. Chem. Int. Ed. 1999, 38, 1993-1996.
30. a) F. Garcia-Tellado, S. Goswami, S.-K. Chang, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1990, 112, 7393-7394;
31. b) F. Garcia-Tellado, J. Albert, A. D. Hamilton, Chem. Commun. 1991, 1761-1762.
32. For related approaches to 4-alkoxy-2,5-diaminopyridines, see: a) D. G. Markees, V. C. Dewey, G. W. Kidder, J. Med. Chem. 1968, 11, 126; b) B. Feibush, A. Figueroa, R. Charles, K. D. Onan, P. Feibush, B. L. Karger, J. Am. Chem. Soc. 1986, 108, 3310-3318; c) M. Kotera, J.-M. Lehn, J.-P. Vigneron, J. Chem. Soc. Chem. Commun. 1994, 197-199.
33. For related approaches to 4-alkoxy-2,5-diaminopyridines, see: a) D. G. Markees, V. C. Dewey, G. W. Kidder, J. Med. Chem. 1968, 11, 126; b) B. Feibush, A. Figueroa, R. Charles, K. D. Onan, P. Feibush, B. L. Karger, J. Am. Chem. Soc. 1986, 108, 3310-3318; c) M. Kotera, J.-M. Lehn, J.-P. Vigneron, J. Chem. Soc. Chem. Commun. 1994, 197-199.
34. For related approaches to 4-alkoxy-2,5-diaminopyridines, see: a) D. G. Markees, V. C. Dewey, G. W. Kidder, J. Med. Chem. 1968, 11, 126; b) B. Feibush, A. Figueroa, R. Charles, K. D. Onan, P. Feibush, B. L. Karger, J. Am. Chem. Soc. 1986, 108, 3310-3318; c) M. Kotera, J.-M. Lehn, J.-P. Vigneron, J. Chem. Soc. Chem. Commun. 1994, 197-199.
35. S. Rajeswari, R. J. Jones, M. P. Cava, Tetrahedron Lett. 1987, 28, 5099-5102.
36. L. A. Carpino, D. Sadat-Aalaee, H. G. Chao, R. H. DeSelms, J. Am. Chem. Soc. 1990, 112, 9651-9652.
37. a) A. Furka, F. Sebestyen, M. Asgedom, G. Dibo, Int. J. Pept. Prot. Res. 1991, 36, 487-493;
38. b) K. S. Lam, S. E. Salmon, E. M. Hersh, V. J. Hruby, W. M. Kazmierski, R. J. Knapp, Nature 1991, 354, 82-84.
39. We have previously observed that these amide bonds of the diamidopyridine are susceptible to weakly basic hydrolysis conditions normally suitable for methyl ester hydrolysis, see: C. P. Waymark, J. D. Kilburn, I. Gillies, Tetrahedron Lett. 1995, 36, 3051-3054.
40. a) M. S. Bernatowicz, S. B. Daniels, H. Köster, Tetrahedron Lett. 1989, 30, 4645-4648;
41. b) H. Rink, Tetrahedron Lett. 1987, 28, 3787-3790.
42. DNS-Glu(OtBu)-Ser(tBu)-Val-OH was chosen for initial screening experiments as it was already available in the laboratory.
43. P. Edman, G. Begg, Eur. J. Biochem. 1967, 1, 80-91. Sequencing was performed using an Applied Biosystems 477A pulsed liquid phase sequencer coupled on-line to an Applied Biosystems 120A Phenylthiohydantoin (PTH)-derivative analyser.
44. P. Sieber, Tetrahedron Lett. 1987, 28, 2107-2110.
45. The binding constant was calculated by fitting the data to a 1:1 binding isotherm using NMRTit HG software, kindly provided by Prof. C. A. Hunter. University of Sheffield; see: A. P. Bisson, C. A. Hunter, J. C. Morales, K. Young, Chem. Eur. J. 1998, 4, 845-851.
46. Ac-L-Lys(DNS)-D-Ala-D-Ala-OH was chosen because of its biological relevance as a bacterial cell wall precursor; see: H. C. Neu, Science 1992, 257, 1064-1073.
47. W. F. deGrado, E. T. Kaiser, J. Org. Chem. 1980, 45, 1295.
48. M. D. Weingarten, K. Sekanina, W. C. Still, J. Am. Chem. Soc. 1998, 120, 9112-9113.
49. E. J. Iorio, W. C. Still, Bioorg. Med. Chem. Lett. 1999, 9, 2145-2150; C.-T. Chen, H. Wagner, W. C. Still, Science 1998, 279, 851-853.
50. E. J. Iorio, W. C. Still, Bioorg. Med. Chem. Lett. 1999, 9, 2145-2150; C.-T. Chen, H. Wagner, W. C. Still, Science 1998, 279, 851-853.
51. S. E. Schneider, S. N. O'Neil, E. V. Anslyn, J. Am. Chem. Soc. 2000, 122, 542-543.