The Phenylacetyl Group - The First Amino Protecting Group That Can Be Removed Enzymatically from Oligonucleotides in Solution and on a Solid Support

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 6, 1997, Pages 647-649

  Waldmann, Herbert ^a   Reidel, Armin ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Combinatorial chemistry; Enzymes; Nucleotides; Protecting groups; Solid phase synthesis

Indexed keywords

EID: 0030933632     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199706471     Document Type: Article

References (41)

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11. For recent developments, see a) Y. Hayakawa, S. Wakabayashi, H. Kato, R. Noyori, J. Am. Chem. Soc. 1990, 112, 1691-1696; b) K. P. Stengele, W. Pfeiderer, Tetrahedron Lett. 1990, 31, 2549-2552; c) R. Eritja, J. Robles, A. Avino, F. Albericio, E. Pedroso, Tetrahedron 1992, 48, 4171-4182, and references therein.
12. Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2057-2083; b) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911-937.
13. Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2057-2083; b) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911-937.
14. Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2057-2083; b) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911-937.
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16. a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
17. b) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, ibid. 1996, 108, 82-85 and 1996, 35, 106-109.
18. b) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, ibid. 1996, 108, 82-85 and 1996, 35, 106-109.
19. P. Braun, H. Waldmann, H. Kunz, Bioorg. Med. Chem. 1993, 1, 197-207.
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21. T. Pohl, H. Waldmann, Angew. Chem. 1996, 108, 1829-1832; Angew. Chem. Int. Ed. Engl. 1996, 35, 1720-1723.
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23. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437-2488; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337;
24. Reviews: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2437-2488; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337;
25. b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19-46 and 1996, 35, 17-42.
26. b) J. S. Früchtel, G. Jung, ibid. 1996, 108, 19-46 and 1996, 35, 17-42.
27. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
28. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
29. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
30. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
31. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
32. Only a few enzymatic transformations (mostly glycosylations) have been described: a) D. T. Elmore, D. J. S. Guthrie, A. D. Wallace, S. R. E. Bates, J. Chem. Soc. Chem. Commun. 1992, 1033-1034; b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135-1136; c) R. L. Halcomb, H. Huang, C.-H. Wong, ibid. 1994, 116, 11315-11322; d) S. Köpper, Carbohydr. Res. 1994, 265, 161-166; e) M. Meldal, F.-I. Auzanneau, O. Hindsgaul, M. M. Palcic, J. Chem. Soc. Chem. Commun. 1994, 1849-1850; f) K. Yamada, S.-I. Nishimura, Tetrahedron Lett. 1995, 36, 9493-9497.
33. For the use of the PhAc group for the deprotection of peptides, carbohydrates, and nucleosides, see a) H. Waldmann, Liebigs Ann. Chem. 1988, 1175-1180, and references therein; b) H. Waldmann, A. Heuser, A. Reidel, Synlett 1994, 65-67; c) M. A. Dineva, B. Galunsky, V. Kasche, D. D. Petkov, Bioorg. Med. Chem. Lett. 1993, 3, 2781-2784.
34. For the use of the PhAc group for the deprotection of peptides, carbohydrates, and nucleosides, see a) H. Waldmann, Liebigs Ann. Chem. 1988, 1175-1180, and references therein; b) H. Waldmann, A. Heuser, A. Reidel, Synlett 1994, 65-67; c) M. A. Dineva, B. Galunsky, V. Kasche, D. D. Petkov, Bioorg. Med. Chem. Lett. 1993, 3, 2781-2784.
35. For the use of the PhAc group for the deprotection of peptides, carbohydrates, and nucleosides, see a) H. Waldmann, Liebigs Ann. Chem. 1988, 1175-1180, and references therein; b) H. Waldmann, A. Heuser, A. Reidel, Synlett 1994, 65-67; c) M. A. Dineva, B. Galunsky, V. Kasche, D. D. Petkov, Bioorg. Med. Chem. Lett. 1993, 3, 2781-2784.
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39. 2 (75 min) was used for detritylation; 3% iodine in water/pyridine/THF (2/20/75) (10 min) was employed to oxidize the phosphites to the phosphates. Average yields of coupling were determined by measuring the absorption of the DMTr cation at 498 nm released upon deprotection of the corresponding 5′-OH group.
40. This method of analysis was developed since the oligonucleotides that still carry the PhAc-protected nucleobases cannot be analyzed unambiguously by established sequencing techniques.
41. T. Pohl, H. Waldmann, Tetrahedron Lett. 1995, 36, 2963-2967, and references therein.