An enzyme-labile linker group for organic syntheses on solid supports

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1143-1146

  Sauerbrei, Bernd ^a   Jungmann, Volker ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Cleavage reactions; Combinatorial chemistry; Enzyme catalysis; Lipases; Solid phase synthesis

Indexed keywords

EID: 0032482097     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1143::AID-ANIE1143>3.0.CO;2-E     Document Type: Article

References (32)

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2. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288; b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19 and 1996, 35, 17; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
3. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288; b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19 and 1996, 35, 17; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
4. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288; b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19 and 1996, 35, 17; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
5. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288; b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19 and 1996, 35, 17 ; c) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555.
6. Enzyme Catalysis in Organic Synthesis (Eds.: K. Drauz, H. Wald⇒ mann), VCH, Weinheim, 1995.
7. The detachment of peptides and carbohydrates from solid supports by means of a protease or a phosphatase was reported in only few cases: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135; c) K. Yamada, I. Nishimura, Tetrahedron Lett. 1995, 36, 9493.
8. The detachment of peptides and carbohydrates from solid supports by means of a protease or a phosphatase was reported in only few cases: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135; c) K. Yamada, I. Nishimura, Tetrahedron Lett. 1995, 36, 9493.
9. The detachment of peptides and carbohydrates from solid supports by means of a protease or a phosphatase was reported in only few cases: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135; c) K. Yamada, I. Nishimura, Tetrahedron Lett. 1995, 36, 9493.
10. Reviews: a) T. Kappes, H. Waldmann, Liebigs Ann. 1997, 803; b) M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056.
11. Reviews: a) T. Kappes, H. Waldmann, Liebigs Ann. 1997, 803; b) M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056.
12. Reviews: a) T. Kappes, H. Waldmann, Liebigs Ann. 1997, 803; b) M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056.
13. For applications of this concept in protecting group chemistry see: a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259; b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schroeder, J. R. Silvius, ibid. 1997, 109, 2334 and 1997, 36, 2238; c) T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
14. For applications of this concept in protecting group chemistry see: a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259; b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schroeder, J. R. Silvius, ibid. 1997, 109, 2334 and 1997, 36, 2238; c) T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
15. For applications of this concept in protecting group chemistry see: a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259; b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schroeder, J. R. Silvius, ibid. 1997, 109, 2334 and 1997, 36, 2238; c) T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
16. For applications of this concept in protecting group chemistry see: a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259; b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schroeder, J. R. Silvius, ibid. 1997, 109, 2334 and 1997, 36, 2238; c) T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
17. For applications of this concept in protecting group chemistry see: a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259; b) H. Waldmann, M. Schelhaas, E. Nägele, J. Kuhlmann, A. Wittinghofer, H. Schroeder, J. R. Silvius, ibid. 1997, 109, 2334 and 1997, 36, 2238; c) T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702.
18. W. Rapp. in Combinatorial Peptide and Nonpeptide Libraries (Ed.: G. Jung), VCH, Weinheim, 1996, p. 425.
19. -1 this corresponds to an overall yield of 54% for three steps. The loading of the resin 12 with the tetrahydro-β-carbolines was determined analogously.
20. For Pictet - Spengler reactions on polymeric supports see: a) K. Kaljuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211; b) R. Mohan, Y.-L. Chou, M. M. Morrissey, ibid. 1996, 37, 3963; c) S. Hutchins, K. Chapman, ibid. 1996, 37, 4865; c) L. Yang, L. Guo, ibid. 1996, 37, 5041; d) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, ibid. 1996, 37, 5633.
21. For Pictet - Spengler reactions on polymeric supports see: a) K. Kaljuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211; b) R. Mohan, Y.-L. Chou, M. M. Morrissey, ibid. 1996, 37, 3963; c) S. Hutchins, K. Chapman, ibid. 1996, 37, 4865; c) L. Yang, L. Guo, ibid. 1996, 37, 5041; d) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, ibid. 1996, 37, 5633.
22. For Pictet - Spengler reactions on polymeric supports see: a) K. Kaljuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211; b) R. Mohan, Y.-L. Chou, M. M. Morrissey, ibid. 1996, 37, 3963; c) S. Hutchins, K. Chapman, ibid. 1996, 37, 4865; c) L. Yang, L. Guo, ibid. 1996, 37, 5041; d) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, ibid. 1996, 37, 5633.
23. For Pictet - Spengler reactions on polymeric supports see: a) K. Kaljuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211; b) R. Mohan, Y.-L. Chou, M. M. Morrissey, ibid. 1996, 37, 3963; c) S. Hutchins, K. Chapman, ibid. 1996, 37, 4865; c) L. Yang, L. Guo, ibid. 1996, 37, 5041; d) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, ibid. 1996, 37, 5633.
24. For Pictet - Spengler reactions on polymeric supports see: a) K. Kaljuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211; b) R. Mohan, Y.-L. Chou, M. M. Morrissey, ibid. 1996, 37, 3963; c) S. Hutchins, K. Chapman, ibid. 1996, 37, 4865; c) L. Yang, L. Guo, ibid. 1996, 37, 5041; d) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, ibid. 1996, 37, 5633.
25. 3OD, 25° C, TMS): δ = 7.28-7.49 (m, 6H, H-7, H-14-18), 7.12 (dd, 1H, H-10, J = 6.8, J′ = 1.4 Hz), 6.96 (td, 1H, H-9, J = 6.9, J′ = 1.3 Hz), 6.90 (td, 1H, H-8, J = 6.9, J′ = 1.4 Hz), 5.99 (br. s, 1H, H-1 (trans)), 5.84 (br. s, 1H, H-1 (cis)), 4.12-4.26 (m, 1H, H-3), 3.35-3.51 (br. m, 2H, H-4).
26. G. Le Corre, E. Guibé-Jampel, M. Wakselman, Tetrahedron 1978, 34, 3105.
27. If an amino group can function intramolecularly as nucleophile, the fragmentation (in these cases with cyclization) can occur even at pH 8. This principle can also be employed for the development of an anchor group that can be cleaved by classical chemical methods: B. Atrash, M. Bradley, J. Chem. Soc. Chem. Commun. 1997, 1397.
28. [3] and a) R. L. Halcomb, H. Huang, C-H. Wong, J. Am. Chem. Soc. 1994, 116, 11315; b) S. Köpper, Carbohydr. Res. 1994, 265, 161; c) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849; d) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642; Angew. Chem. Int. Ed. Engl. 1997, 36, 647.
29. [3] and a) R. L. Halcomb, H. Huang, C-H. Wong, J. Am. Chem. Soc. 1994, 116, 11315; b) S. Köpper, Carbohydr. Res. 1994, 265, 161; c) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849; d) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642; Angew. Chem. Int. Ed. Engl. 1997, 36, 647.
30. [3] and a) R. L. Halcomb, H. Huang, C-H. Wong, J. Am. Chem. Soc. 1994, 116, 11315; b) S. Köpper, Carbohydr. Res. 1994, 265, 161; c) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849; d) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642; Angew. Chem. Int. Ed. Engl. 1997, 36, 647.
31. [3] and a) R. L. Halcomb, H. Huang, C-H. Wong, J. Am. Chem. Soc. 1994, 116, 11315; b) S. Köpper, Carbohydr. Res. 1994, 265, 161; c) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849; d) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642; Angew. Chem. Int. Ed. Engl. 1997, 36, 647.
32. [3] and a) R. L. Halcomb, H. Huang, C-H. Wong, J. Am. Chem. Soc. 1994, 116, 11315; b) S. Köpper, Carbohydr. Res. 1994, 265, 161; c) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849; d) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642; Angew. Chem. Int. Ed. Engl. 1997, 36, 647.