A Reinvestigation of the Preparation, Properties, and Applications of Aminomethyl and 4-Methylbenzhydrylamin

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3706-3716

  Howard Adams, J ^a   Cook, Ronald M ^a   Hudson, Derek ^a   Jammalamadaka, Vasu ^a,b   Lyttle, Matthew H ^a   Songster, Michael F ^a  

^a Solid Phase Sciences   (United States)

^b SIDDCO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542392912     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9802269     Document Type: Article

References (51)

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2. Review: Songster, M. F.; Barany, G. Methods Enzymol. 1997, 289, 126-174.
3. Cook, R. M.; Adams, J. H.; Hudson, D. Tetrahedron Lett. 1994, 35, 6777-6780.
4. Review: Barany, G.; Albericio, F.; Kates, S. A.; Kemp, M. Polym. Prepr., Am. Chem. Soc. Div. Polym. Chem. 1997, in press.
5. Matsueda, G. R.; Stewart, J. M. Peptides 1981, 2, 45-50.
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13. (b) Truchlik, S.; Macko, J.; Mojik, I.; Bytricky, L.; Dulak, K.; Paldan, M.; Handlovsky, A. CS Patent 248 250, 1988; Chem. Abstr. 1988, 110, 75315.
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20. The PEG-PS graft copolymers have been assigned the following trade names: Champion I (8), Champion II (9), and Dendrogel (10).
21. Solvation of peptide resin matrices has been studied in a wide range of solvents, see: (a) Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202. (b) Cilli, E. M.; Oliveira, E.; Marchetto, R.; Nakaie, C. R. J. Org. Chem. 1996, 61, 8992-9000.
22. Solvation of peptide resin matrices has been studied in a wide range of solvents, see: (a) Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202. (b) Cilli, E. M.; Oliveira, E.; Marchetto, R.; Nakaie, C. R. J. Org. Chem. 1996, 61, 8992-9000.
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24. Meister, S. M.; Kent, S. B. H. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; pp 103-106.
25. The original publication describing synthetic difficulties with acyl carrier protein 65-74 was: Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774-781. Improved protocols were later described on polyacrylamide based supports: Arshady, R.; Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans, 1 1981, 529-537. Other studies showed that, for Boc chemistry, implementing coupling in DMF was the primary modification necessary: Live, D. H.; Kent, S. B. H. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; 65-68. This observation was later confirmed by detailed study with Fmoc chemistry on polystyrene (see ref 19). Nevertheless, this sequence still poses significant challenges; see, for example: Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Methods Enzymol. 1997, 289, 14-29 and other examples in this volume.
26. The original publication describing synthetic difficulties with acyl carrier protein 65-74 was: Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774-781. Improved protocols were later described on polyacrylamide based supports: Arshady, R.; Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans, 1 1981, 529-537. Other studies showed that, for Boc chemistry, implementing coupling in DMF was the primary modification necessary: Live, D. H.; Kent, S. B. H. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; 65-68. This observation was later confirmed by detailed study with Fmoc chemistry on polystyrene (see ref 19). Nevertheless, this sequence still poses significant challenges; see, for example: Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Methods Enzymol. 1997, 289, 14-29 and other examples in this volume.
27. The original publication describing synthetic difficulties with acyl carrier protein 65-74 was: Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774-781. Improved protocols were later described on polyacrylamide based supports: Arshady, R.; Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans, 1 1981, 529-537. Other studies showed that, for Boc chemistry, implementing coupling in DMF was the primary modification necessary: Live, D. H.; Kent, S. B. H. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; 65-68. This observation was later confirmed by detailed study with Fmoc chemistry on polystyrene (see ref 19). Nevertheless, this sequence still poses significant challenges; see, for example: Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Methods Enzymol. 1997, 289, 14-29 and other examples in this volume.
28. The original publication describing synthetic difficulties with acyl carrier protein 65-74 was: Hancock, W. S.; Prescott, D. J.; Vagelos, P. R.; Marshall, G. R. J. Org. Chem. 1973, 38, 774-781. Improved protocols were later described on polyacrylamide based supports: Arshady, R.; Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans, 1 1981, 529-537. Other studies showed that, for Boc chemistry, implementing coupling in DMF was the primary modification necessary: Live, D. H.; Kent, S. B. H. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; 65-68. This observation was later confirmed by detailed study with Fmoc chemistry on polystyrene (see ref 19). Nevertheless, this sequence still poses significant challenges; see, for example: Alewood, P.; Alewood, D.; Miranda, L.; Love, S.; Meutermans, W.; Wilson, D. Methods Enzymol. 1997, 289, 14-29 and other examples in this volume.
29. Lyttle, M. H.; Hudson, D. In Peptides: Chemistry and Biology: Proceedings of the Twelfth American Peptide Symposium; Smith, J. A., Rivier, J. E., Eds.; ESCOM: Leiden, The Netherlands, 1992; pp 583-584.
30. Vágner, J.; Krchňák, V.; Sepetov, N. F.; Štrop, P.; Lam, K. S.; Barany, G.; Lebl, M. In Innovations and Perspectives in Solid-Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications, 1994: Collected Papers, Third International Symposium; Epton, R., Ed.; Mayflower Worldwide: Birmingham, England, 1994; pp 347-352.
31. Reddy, M. P.; Michael, M. A.; Farooqui, F.; Girgis, N. S. Tetrahedron Lett. 1994, 35, 5771-5774.
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33. (a) Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997-10998.
34. (b) Bunin, B. A.; Plunkett, M. J.; Ellman, J. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4708-4712.
35. Reports have described improvement in peptide synthesis using DMSO on a highly loaded benzhydrylamine resin, even though the starting resin did not swell in this solvent; see: Marchetto, R.; de Oliveira, E.; Paiva, A. C. M.; Nakaie, C. R. In Peptides 1990: Proceedings of the Twenty-First European Peptide Symposium; Giralt, E., Andreu, D., Eds.; ESCOM: Leiden, The Netherlands, 1990; pp 122-124.
36. (a) Bodanszky, M.; Deshmane, S. S.; Martinez, J. J. Org. Chem. 1979, 44, 1622.
37. (b) Bodanszky, A.; Bodanszky, M.; Chandramouli, N.; Kwei, J. Z.; Martinez, J.; Tolle, J. C. J. Org. Chem. 1980, 45, 72.
38. Burgess, K.; Lim, D. J. Chem Soc., Chem. Commun. 1997, 785-786; also see ref 38.
39. Review: Meldal, M. Methods Enzymol. 1997, 289, 83-104.
40. (a) Bayer, E.; Hemmasi, B.; Albert, K.; Rapp, W.; Dengler, M. In Peptides: Structure and Function: Proceedings of the Eighth American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce: Rockford, IL, 1983; pp 87-90.
41. (b) Rapp, W.; Zhang, L.; Häbich, R.; Bayer, E. In Peptides 1988: Proceedings of the Twentieth European Peptide Symposium; Jung, G., Bayer, E., Eds.; de Gruyter: Berlin, Germany, 1989; pp 199-201.
42. Gooding, O.; Hoeprich, P. D. J.; Labadie, J. W.; Porco, J. A. J.; van Eikeren, P.; Wright, P. In Molecular Diversity and Combinatorial Chemistry Libraries and Drug Discovery; Chaiken, I. M., Janda, K. D., Eds.; American Chemical Society: Washington, DC, 1996; p 199.
43. Zalipsky, S.; Chang, J. L.; Albericio, F.; Barany, G. React. Polym. 1994, 22, 243 and references therein.
44. Ho, D. D.; Neumann, A. V.; Perelson, A. S.; Chen, W.; Leonard, J. M.; Markowitz, M. Nature 1995, 373, 123.
45. Barany, G.; Sole, N. A.; van Abel, R. J.; Albericio, F.; Selsted, M. E. In Innovations and Perspectives in Solid-Phase Synthesis: Peptides, Polypeptides and Oligonucleotides, 1992: Collected Papers, Second International Symposium; Epton, R., Ed.; Intercept: Andover, England, 1992; pp 29-38.
46. Aldrich, J. V.; Leelasvatanakij, L.; Maeda, D. Y. In Peptides: Chemistry, Structure and Biology: Proceedings of the Fourteenth American Peptide Symposium; Kaumaya, J. T. P., Hodges, R. S., Eds.; Mayflower Scientific: Kingswinford, U.K., 1996; pp 36-38.
47. Resin 10b has proved an efficient support for the assembly of a variety of complex peptide - DNA hybrids: Songster, M. F. Solid Phase Sciences, unpublished results.
48. Ruhland, B.; Bombrun, A.; M. Gallop, M. A. J. Org. Chem. 1997, 62, 7820-7826.
49. 3 at 55 °C for 6 h.
50. In addition to the detailed experiments presented, resin 8 has been used to synthesize many complex biomolecules, including a 68-residue peptide, and a variety of unmodified and fluorescently labeled DNA sequences.
51. Krchňák, V.; Weichsel, A. S.; Cabel, D.; Flegelová, Z.; Lebl, M. Mol. Diversity 1996, 1, 149.