Chemoenzymatic synthesis of nucleopeptides

Chemistry - A European Journal

Volumn 5, Issue 2, 1999, Pages 669-681

  Flohr, Stefanie ^a   Jungmann, Volker ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Bioorganic chemistry; Enzyme catalysis; Nucleopeptides; Nucleotides; Protecting groups

Indexed keywords

NUCLEOPROTEIN; PEPTIDE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; PEPTIDE SYNTHESIS; SOLUBILIZATION; VIRUS REPLICATION;

EID: 0033004827     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990201)5:2<669::AID-CHEM669>3.0.CO;2-V     Document Type: Article

References (66)

1. a) B. A. Juodka, Nucleosides Nucleotides 1984, 3, 445-483;
2. b) J. C. Wang, Ann. Rev. Biochem. 1985, 54, 665-697;
3. c) A. B. Vartapetian, A. A. Bogdanov, Prog. Nucleic Acid Res. Mol. Biol. 1987, 34, 209-251;
4. d) T. J. Kelly, M. S. Wold, J. Li, Adv. Virus Res. 1988, 34, 1-42;
5. d) M. Salas in The Viruses, Vol. 1 The Bacteriophages (Ed.: R. Calender).
6. K. A. Henningfeld, T. Arslan, S. M. Hecht, J. Am. Chem. Soc. 1996, 118, 11701-11714.
7. a) Review: M. Salas, Ann. Rev. Biochem. 1991, 160, 39-71;
8. b) Review: M. Salas, Virus Strategies - Molecular Biology and Pathogenesis, VCH, Weinheim, 1993, pp. 1-23;
9. c) L. Blanco, J. M. Lázaro, M. de Vega, A. Bonnin, M. Salas, Proc. Natl. Acad. Sci. 1994, 91, 12198.
10. For a recent review on the synthesis of nucleotides, which also addresses the problems encountered in the removal of the blocking functions see: S. L. Beaucage, R. P. Iyer, Tetrahedron 1992, 48, 2223-2311.
11. a) B. Juodka, V. Kirveliene, P. Povilionis, Nucleosides & Nucleotides 1982, 1, 497-508;
12. b) E. Kuyl-Yeheskiely, P. A. M. van der Klein, G. M. Visser, G. A. van der Marel, J. H. van Boom, Recl. Trav. Chim. Pays-Bas 1986, 105, 69-70.
13. a) E. Kuyl-Yeheskiely, C. M. Tromp, A. W. M. Lefeber, G. A. van der Marel, J. H. van Boom, Tetrahedron 1988, 44, 6515-6523;
14. b) E. Kuyl-Yeheskiely, C. M. Dreef-Tromp, A. Geluk, G. A. van der Marel, J. H. van Boom, Nucleic Acids Res. 1989, 17, 2897-2905;
15. c) C. M. Dreef-Tromp, J. C. M. van der Marel, H. van den Elst, G. A. van der Marel, J. H. van Boom, Nucleic Acids Res. 1992, 20, 4015-4020;
16. d) Y. Ueno, R. Saito, T. Hata, Nucleic Acids Res. 1993, 21, 4451-4457;
17. e) J. Robles, E. Pedroso, A. Grandas, Tetrahedron Lett. 1994, 35, 4449-4452;
18. f) J. Robles, E. Pedroso, A. Grandas, J. Org. Chem. 1994, 59, 2482-2486.
19. Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056;
20. Reviews: a) H. Waldmann, M. Schelhaas, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056;
21. b) H. Waldmann, D. Sebastian, Chem. Rev. 1994, 94, 911-937.
22. a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
23. a) H. Waldmann, E. Nägele, Angew. Chem. 1995, 107, 2425-2428; Angew. Chem. Int. Ed. Engl. 1995, 34, 2259-2262;
24. b) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, Angew. Chem. 1996, 108, 82-85; Angew. Chem. Int. Ed. Engl. 1996, 35, 106-109;
25. b) M. Schelhaas, S. Glomsda, M. Hänsler, H.-D. Jakubke, H. Waldmann, Angew. Chem. 1996, 108, 82-85; Angew. Chem. Int. Ed. Engl. 1996, 35, 106-109;
26. c) H. Waldmann, M. Schelhaas, E. Nagele, J. Kuhlmann, A. Wittighofer, H. Schroeder, J. R. Silvius, Angew. Chem. 1997, 709, 2334-2337; Angew. Chem. Int. Ed. Engl. 1997, 36, 2238-2241.
27. c) H. Waldmann, M. Schelhaas, E. Nagele, J. Kuhlmann, A. Wittighofer, H. Schroeder, J. R. Silvius, Angew. Chem. 1997, 709, 2334-2337; Angew. Chem. Int. Ed. Engl. 1997, 36, 2238-2241.
28. a) T. Pohl, H. Waldmann, Angew. Chem. 1996, 108, 1829-1832; Angew. Chem. Int. Ed. Engl. 1996, 35, 1720-1723;
29. a) T. Pohl, H. Waldmann, Angew. Chem. 1996, 108, 1829-1832; Angew. Chem. Int. Ed. Engl. 1996, 35, 1720-1723;
30. b) P. Braun, H. Waldmann, H. Kunz, Bioorg. Med. Chem. 1993, 1, 197-207; T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702-6710.
31. b) P. Braun, H. Waldmann, H. Kunz, Bioorg. Med. Chem. 1993, 1, 197-207; T. Pohl, H. Waldmann, J. Am. Chem. Soc. 1997, 119, 6702-6710.
32. a) H. Waldmann, A. Heuser, S. Schulze, Tetrahedron Lett. 1996, 37, 8725-8728;
33. b) H. Waldmann, D. Sebastian, Tetrahedron Lett. 1997, 38, 2927-2930;
34. c) D. Sebastian, A. Heuser, S. Schulze, H. Waldmann, Synthesis 1997, 1098-1108.
35. Parts of the results reported here were published in preliminary form: a) H. Waldmann, S. Gabold, Chem. Comm. 1997, 79, 1861-1862;
36. b) V. Jungmann, H. Waldmann, Tetrahedron Lett. 1998, 39, 1139-1142.
37. a) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642-644; Angew. Chem. Int. Ed. Engl. 1997, 36, 647-649;
38. a) H. Waldmann, A. Reidel, Angew. Chem. 1997, 109, 642-644; Angew. Chem. Int. Ed. Engl. 1997, 36, 647-649;
39. b) M. A. Dineva, B. Galunsky, V. Kasche, D. D. Petkov, Bioorg. Med. Chem. Lett. 1993, 3, 2781-1784.
40. a) K. L. Agarwal, A. Yamazaki, P. J. Cashion, H. G. Khorana, Angew. Chem. 1972, Angew. Chem. Int. Ed. Engl. 1972, 11, 451-459;
41. a) K. L. Agarwal, A. Yamazaki, P. J. Cashion, H. G. Khorana, Angew. Chem. 1972, Angew. Chem. Int. Ed. Engl. 1972, 11, 451-459;
42. b) H. Schaller, G. Weinmann, B. Lerch, H. G. Khorana, J. Am. Chem. Soc. 1963, 85, 3821-3827.
43. M. D. Matteucci, M. H. Caruthers, Tetrahedron Lett. 1980, 27, 3243-3246.
44. W. Bannwarth, E. Küng, Tetrahedron Lett. 1989, 30, 4219-4222.
45. For the enzymatic removal of methyl esters from glycosylated amino acids see: a) D. Cantacuzene, S. Attal, S. Bay, Bioorg. Med. Chem. Lett. 1991, 1, 197-200;
46. b) S. Attal, S. Bay, D. Cantacuzene, Tetrahedron 1992, 48, 9251-9260;
47. c) H. Ishii, K. Unabashi, Y. Mimura, Y. Inoue, Bull. Chem. Soc. Jpn. 1990, 63, 3042-3043.
48. For the enzymatic removal of MEE esters from glycosylated amino acids and glycopeptides see: J. Eberling, P. Braun, D. Kowalczyk, M. Schultz, H. Kunz, J. Org. Chem. 1996, 61, 2638-2646.
49. E. P. Sonnet, M. W. Baillargeon, Lipids 1991, 26, 295-300.
50. a) E. M. Kosower, B. Pazhenchevsky, J. Am. Chem. Soc. 1980, 102, 4983-4988;
51. b) S. Shaninian, J. R. Silvius, Biochem. 1995, 34, 3812-3816;
52. c) E. M. Kosower, B. Pazhenchevsky, H. Doduk, H. Klanety, D. Faust, J. Org. Chem. 1981, 46, 1666-1671.
53. G. Braum, P. Braun, D. Kowalczyk, H. Kunz, Tetrahedron Lett. 1993, 34, 3111-3114.
54. M. Dessolin, M.-G. Guillerez, N. Thieriet, F. Guibé, A. Loffet, Tetrahedron Lett. 1995, 36, 5741-5744.
55. a) Y. Hayakawa, M. Hirose, R. Noyori, J. Org. Chem. 1993, 58, 5551-5555;
56. b) Y. Hayakawa, M. Uchiyama, H. Kato, R. Noyori, Tetrahedron Lett. 1985, Vol. 26 No. 52, 6505-6508.
57. For the undesired attack of proteases on peptide bonds during enzymatic removal of blocking functions from peptides see the references given in ref. [7b], in particular a) E. Walton, J. O. Rodin, C. H. Stammer, F. W. Holly, J. Org. Chem. 1962, 27, 2255;
58. b) G. Kloss, E. Schröder, Hoppe-Seyler's Z. Physiol. Chem. 1964, 336, 248.
59. a) M. Buchholz, H. Kunz, Liebigs Ann. Chem. 1983, 1859-1885;
60. b) H. Kunz, M. Buchholz, Chem. Ber. 1979, 112, 2145-2157.
61. L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
62. J. S. Ralston, A. R. Main, B. F. Kilpatrick, A. L. Chasson, Biochem. J. 1983, 211, 243-250.
63. P. Schultheiss-Reimann, H. Kunz, Angew. Chem. 1983, 95, 64; Angew. Chem. Int. Ed. Eng. 1983, 22, 62.
64. P. Schultheiss-Reimann, H. Kunz, Angew. Chem. 1983, 95, 64; Angew. Chem. Int. Ed. Eng. 1983, 22, 62.
65. J. E. Smart, B. W. Stillmann, J. Biol. Chem. 1982, 257, 13499-13506.
66. W. Bannwarth, E. Küng, Tetrahedron Lett. 1989, 30, 4219-4222.