Generalized dipeptidomimetic template: Solution phase parallel synthesis of combinatorial libraries

Journal of the American Chemical Society

Volumn 118, Issue 8, 1996, Pages 2109-2110

  Boger, Dale L ^a   Tarby, Christine M ^b   Myers, Peter L ^b   Caporale, Lynn Helena ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b Formerly CombiChem Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0029987185     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9539711     Document Type: Article

References (24)

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11. Frank, R. Bioorg Med. Chem Lett. 1993, 3, 425. Frank, R : During, R. Tetrahedron 1988, 44, 6031. Schmidt, M.; Eichler, J.; Odarjuk, J.; Krause, E.; Beyermann, M.; Bienert, M. Bioorg. Med Chem. Lett 1993, 3, 441. Eichler, J.; Bienert, M.; Stierandova, A.; Lebl. M. Pept. Res 1991, 4, 296.
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14. Panlabs have disclosed but not yet detailed a single-step parallel synthesis of rndividual compounds using reliable solution chemistry, and three groups have disclosed solution phase, single-step amide, ester, or carbamate condensations for the preparation of library, mixtures Peterson, J. B In Exploiting Molecular Dtversiry: Small Molecule Libraries for Drug Discovery; La Jolla, CA, January 23-25, 1995. Smith. P. W , Lai, J. Y Q.: Whittington, A. R.: Cox, B : Houston, J G ; Stylli, C. H., Banks, M. N., Tiller, P R. Bioorg. Med. Chem. Lett 1994, 4, 2821. Pirrung, M. C.: Chen. J. J. Am. Chem. Soc 1995, 117, 1240 Carell, T ; Wintner, E A.: Bashir-Hashemi, A., Rebek, J., Jr. Angew. Chem., Int. Ed Engl. 1994. 33, 2059. For the introduction of soluble polymer supports, see Hun. H.; Wolfe, M. M.: Brenner, S., Janda, K. D. Proc. Natl. Acad. Sci. U S A. 1995, 92. 6419.
15. Panlabs have disclosed but not yet detailed a single-step parallel synthesis of rndividual compounds using reliable solution chemistry, and three groups have disclosed solution phase, single-step amide, ester, or carbamate condensations for the preparation of library, mixtures Peterson, J. B In Exploiting Molecular Dtversiry: Small Molecule Libraries for Drug Discovery; La Jolla, CA, January 23-25, 1995. Smith. P. W , Lai, J. Y Q.: Whittington, A. R.: Cox, B : Houston, J G ; Stylli, C. H., Banks, M. N., Tiller, P R. Bioorg. Med. Chem. Lett 1994, 4, 2821. Pirrung, M. C.: Chen. J. J. Am. Chem. Soc 1995, 117, 1240 Carell, T ; Wintner, E A.: Bashir-Hashemi, A., Rebek, J., Jr. Angew. Chem., Int. Ed Engl. 1994. 33, 2059. For the introduction of soluble polymer supports, see Hun. H.; Wolfe, M. M.: Brenner, S., Janda, K. D. Proc. Natl. Acad. Sci. U S A. 1995, 92. 6419.
16. Panlabs have disclosed but not yet detailed a single-step parallel synthesis of rndividual compounds using reliable solution chemistry, and three groups have disclosed solution phase, single-step amide, ester, or carbamate condensations for the preparation of library, mixtures Peterson, J. B In Exploiting Molecular Dtversiry: Small Molecule Libraries for Drug Discovery; La Jolla, CA, January 23-25, 1995. Smith. P. W , Lai, J. Y Q.: Whittington, A. R.: Cox, B : Houston, J G ; Stylli, C. H., Banks, M. N., Tiller, P R. Bioorg. Med. Chem. Lett 1994, 4, 2821. Pirrung, M. C.: Chen. J. J. Am. Chem. Soc 1995, 117, 1240 Carell, T ; Wintner, E A.: Bashir-Hashemi, A., Rebek, J., Jr. Angew. Chem., Int. Ed Engl. 1994. 33, 2059. For the introduction of soluble polymer supports, see Hun. H.; Wolfe, M. M.: Brenner, S., Janda, K. D. Proc. Natl. Acad. Sci. U S A. 1995, 92. 6419.
17. Panlabs have disclosed but not yet detailed a single-step parallel synthesis of rndividual compounds using reliable solution chemistry, and three groups have disclosed solution phase, single-step amide, ester, or carbamate condensations for the preparation of library, mixtures Peterson, J. B In Exploiting Molecular Dtversiry: Small Molecule Libraries for Drug Discovery; La Jolla, CA, January 23-25, 1995. Smith. P. W , Lai, J. Y Q.: Whittington, A. R.: Cox, B : Houston, J G ; Stylli, C. H., Banks, M. N., Tiller, P R. Bioorg. Med. Chem. Lett 1994, 4, 2821. Pirrung, M. C.: Chen. J. J. Am. Chem. Soc 1995, 117, 1240 Carell, T ; Wintner, E A.: Bashir-Hashemi, A., Rebek, J., Jr. Angew. Chem., Int. Ed Engl. 1994. 33, 2059. For the introduction of soluble polymer supports, see Hun. H.; Wolfe, M. M.: Brenner, S., Janda, K. D. Proc. Natl. Acad. Sci. U S A. 1995, 92. 6419.
18. Panlabs have disclosed but not yet detailed a single-step parallel synthesis of rndividual compounds using reliable solution chemistry, and three groups have disclosed solution phase, single-step amide, ester, or carbamate condensations for the preparation of library, mixtures Peterson, J. B In Exploiting Molecular Dtversiry: Small Molecule Libraries for Drug Discovery; La Jolla, CA, January 23-25, 1995. Smith. P. W , Lai, J. Y Q.: Whittington, A. R.: Cox, B : Houston, J G ; Stylli, C. H., Banks, M. N., Tiller, P R. Bioorg. Med. Chem. Lett 1994, 4, 2821. Pirrung, M. C.: Chen. J. J. Am. Chem. Soc 1995, 117, 1240 Carell, T ; Wintner, E A.: Bashir-Hashemi, A., Rebek, J., Jr. Angew. Chem., Int. Ed Engl. 1994. 33, 2059. For the introduction of soluble polymer supports, see Hun. H.; Wolfe, M. M.: Brenner, S., Janda, K. D. Proc. Natl. Acad. Sci. U S A. 1995, 92. 6419.
19. For a 10000-member library (three-step synthesis at 95% yietd/step) to obtain 50 mg of each component (MW = 500 g/mol) on Memfield resin with a typical loading of 1 mmol/g requires 1 166 kg of solid support = S2449/library. on Wang resin with J loading of 0.7 mmol/g. it requires 1.666 kg of solid support = S8331/library
20. Egner, B J : Langle, G J., Bradley. M. J Org. Chem 1995. 60, 2652. Anderson, R C.; Jarema, M. A.: Shapiro, M J , Stokes, J P , Zihox, M. J Org Chem. 1995, 60, 2650. Fitch. W. L., Detre, G., Holmes, C P.; Shoolery, J. N : Keifer, P A. J. Org. Chem. 1994, 59, 7955. Look, G C., Holmes, C. P . Chinn, J. P . Gallop, M A. J Org Chem 1994. 59, 7588.
21. Egner, B J : Langle, G J., Bradley. M. J Org. Chem 1995. 60, 2652. Anderson, R C.; Jarema, M. A.: Shapiro, M J , Stokes, J P , Zihox, M. J Org Chem. 1995, 60, 2650. Fitch. W. L., Detre, G., Holmes, C P.; Shoolery, J. N : Keifer, P A. J. Org. Chem. 1994, 59, 7955. Look, G C., Holmes, C. P . Chinn, J. P . Gallop, M A. J Org Chem 1994. 59, 7588.
22. Egner, B J : Langle, G J., Bradley. M. J Org. Chem 1995. 60, 2652. Anderson, R C.; Jarema, M. A.: Shapiro, M J , Stokes, J P , Zihox, M. J Org Chem. 1995, 60, 2650. Fitch. W. L., Detre, G., Holmes, C P.; Shoolery, J. N : Keifer, P A. J. Org. Chem. 1994, 59, 7955. Look, G C., Holmes, C. P . Chinn, J. P . Gallop, M A. J Org Chem 1994. 59, 7588.
23. Egner, B J : Langle, G J., Bradley. M. J Org. Chem 1995. 60, 2652. Anderson, R C.; Jarema, M. A.: Shapiro, M J , Stokes, J P , Zihox, M. J Org Chem. 1995, 60, 2650. Fitch. W. L., Detre, G., Holmes, C P.; Shoolery, J. N : Keifer, P A. J. Org. Chem. 1994, 59, 7955. Look, G C., Holmes, C. P . Chinn, J. P . Gallop, M A. J Org Chem 1994. 59, 7588.
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