Stepwise solid phase synthesis of uridylylated viral genome-linked peptides using uridylylated amino acid building blocks

Tetrahedron

Volumn 59, Issue 9, 2003, Pages 1589-1597

  Kriek, Nicole M A J ^a   Filippov, Dmitri V ^a   Van Den Elst, Hans ^a   Meeuwenoord, Nico J ^a   Tesser, Godefridus I ^b   Van Boom, Jacques H ^a   Van Der Marel, Gijs A ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Genome linked peptides; Rink Amide resin; Solid phase peptide synthesis; Uridylylated amino acid building blocks

Indexed keywords

2 CYANOETHYL N (9 FLUORENYLMETHOXYCARBONYL)TYROSIN 4 YL(2',3' DI O ACETYLURIDIN 5' YL)PHOSPHATE; BENZENE DERIVATIVE; O (2 CHLOROPHENYL) N (9 FLUORENYLMETHOXYCARBONYL)SERIN 3 YL(2',3' DI O ACETYLURIDIN 5' YL)PHOSPHATE; O (2 CHLOROPHENYL) N (9 FLUORENYLMETHOXYCARBONYLSERIN 3 YLALLYL ESTER)(2',3' DI O ACETYLURIDIN 5' YL)PHOSPHATE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; COWPEA; COXSACKIE VIRUS; GENOME; MOSAIC VIRUS; NONHUMAN; POLIOMYELITIS VIRUS; PRIORITY JOURNAL; SOLID; SYNTHESIS;

COWPEA MOSAIC VIRUS;

EID: 0037463443     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00042-5     Document Type: Article

References (30)

1. Melnick J.L. Fields B.N., Knipe D.M., Howley P.M. Fields Virology. Vol. 1:1996;665-712 Lippncott-Raven, Philadelphia, PA.
2. (a) Lee Y.F., Nomoto A., Detjen B.M., Wimmer E. Proc. Natl Acad. Sci. USA. 74:1977;59-63.
3. (b) Rothberg P.G., Harris T.J.R., Nomoto A., Wimmer E. Proc. Natl Acad. Sci. USA. 75:1978;4868-4872.
4. (c) Kitamura N., Semler B.L., Rothberg P.G., Larsen G.R., Adler C.J., Dorner A.J., Emini E.A., Hanecak R., Lee J.J., van der Werf S., Anderson C.W., Wimmer E. Nature. 291:1981;547-553.
5. Agol V.I., Paul A.V., Wimmer E. Virus Res. 62:1996;129-147.
6. Paul A.V., van Boom J.H., Filippov D., Wimmer E. Nature. 393:1998;280-284.
7. Filippov D., Kuyl-Yeheskiely E., van der Marel G.A., Tesser G.I., van Boom J.H. Tetrahedron Lett. 39:1998;3597-3600.
8. Paul A.V., Rieder E., Kim D.W., van Boom J.H., Wimmer E. J. Virol. 2000;10359-10370.
9. Melchers W.J., Hoenderop J.G., Bruins Slot H.J., Pleij C.W., Pilipenko E.V., Agol V.I., Galama J.M. J. Virol. 71:1997;686-696. and references cited therein.
10. (a) Eggen R., Van Kammen A. Domingo E., Holland J.J., Ahlquist P. RNA Genetics. Vol. 1:1998;49-69 CRC, Boca Raton, FL.
11. (b) Zabel P., Moerman M., Lomonossoff G., Shanks M., Beyreuter K. EMBO J. 3:1984;1629-1634.
12. Pon R.T. Tetrahedron Lett. 28:1987;3643-3646.
13. Meldal M., Bielfeldt T., Peters S., Jensen K.J., Paulsen H., Bock K. Int. J. Pept. Protein Res. 43:1994;529-536.
14. Wakamiya T., Saruta K., Yasuoka J., Kusumoto S. Chem. Lett. 1994;1099-1102.
15. (a) Chang C.-D., Waki M., Ahmad M., Meienhofer J., Lundell E.O., Haug J.D. Int. J. Pept. Protein Res. 15:1980;59-66.
16. (b) Robles J., Beltran V., Pérez Y., Travesset I., Pedroso E., Grandas A. Tetrahedron. 55:1999;13251-13264.
17. (a) Shabarova L.A. Davidson N.J., Cohn W.E. Progress in Nucleic Acids Research and Molecular Biology. Vol. 10:1970;145-182 Academic, London.
18. (b) Juodka B.A. Nucleosides Nucleotides. 3:1984;445-483.
19. (a) Robles J., Pedroso E., Grandas A. Nucleic Acids Res. 23:1995;4151-4161.
20. (b) Zubin E.M., Romanova E.A., Oretskaya T.S. Russ. Chem. Rev. 71:2002;239-264.
21. (a) Kuyl-Yeheskiely E., Tromp C.M., Geluk A., van der Marel G.A., van Boom J.H. Nucleic Acids Res. 17:1989;2897-2905.
22. (b) Kuyl-Yeheskiely E., van der Klein P.A.M., Visser G.M., van der Marel G.A., van Boom J.H. Recl. Trav. Chim. Pays-Bas. 105:1986;69-70.
23. (c) Kuyl-Yeheskiely E., Tromp C.M., Lefeber A.W.M., van der Marel G.A., van Boom J.H. Tetrahedron. 20:1988;6515-6523.
24. It has also been reported that the Fmoc group can be rapidly removed by fluoride ions (i.e. dry TBAF in DMF): Ueki M., Amemiya M. Tetrahedron Lett. 28:1987;6617-6620.
25. It is also of interest to note that the 2-cyanoethyl group, which can also be removed with fluoride ions, has been used earlier to serve the same purpose. See in this respect: (a) Dreef-Tromp C.M., van den Elst H., van der Marel G.A., van Boom J.H. Nucleic Acids Res. 20:1992;4015-4020 Robles J., Pedroso E., Grandas A. Tetrahedron Lett. 35:1994;4449-4452.
26. It is also of interest to note that the 2-cyanoethyl group, which can also be removed with fluoride ions, has been used earlier to serve the same purpose. See in this respect: (a) Dreef-Tromp C.M., van den Elst H., van der Marel G.A., van Boom J.H. Nucleic Acids Res. 20:1992;4015-4020 Robles J., Pedroso E., Grandas A. Tetrahedron Lett. 35:1994;4449-4452.
27. Van der Marel G.A., van Boeckel C.C.A., Wille G., van Boom J.H. Tetrahedron Lett. 22:1981;3887-3890.
28. Dangles O., Guibé F., Balavoine G., Lavielle S., Marquet A. J. Org. Chem. 52:1987;4984-4993.
29. Kenner G.W., Todd A.R., Webb R.F., Weymouth F.J. J. Chem. Soc. 1954;2288-2293.
30. Sihna N.D., Biernat J., McManus J., Köster H. Nucleic Acids Res. 12:1984;4539-4557.