Chemical Deprotection Strategy for the Elaboration of Misacylated Transfer RNA's

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 778-779

  Lodder, Michiel ^a   Golovine, Serguei ^a   Hecht, Sidney M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000248581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962170t     Document Type: Article

References (26)

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7. (g) Mamaev, S. V.; Laikhter, A. L.; Arslan, T.; Hecht, S. M. J. Am. Chem. Soc. 1996, 118, 7243.
8. (a) Hecht, S. M.; Alford, B. L.; Kuroda, Y.; Kitano, S. J. Biol. Chem. 1978, 253, 4517.
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11. (d) Baldini, G.; Martoglio, B.; Schachenmann, A.; Zugliani, C.; Brunner, J. Biochemistry 1988, 27, 7951.
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18. 2d
19. See, however, refs 1a, 2a and Mendel, D.; Ellman, J. A.; Schultz, P. G. J. Am. Chem. Soc. 1991, 113, 2758.
20. This group has been developed by Fraser-Reid and co-workers for the protection of simple organic amines. See (a) Debenham, J. S.; Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 3302. (b) Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 7920.
21. This group has been developed by Fraser-Reid and co-workers for the protection of simple organic amines. See (a) Debenham, J. S.; Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 3302. (b) Madsen, R.; Roberts, C.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 7920.
22. Letsinger, R. L.; Lunsford, W. B. J. Am. Chem. Soc. 1976, 98, 3655.
23. Bodanszky, M.; Bodanszky, A. In The Practice of Peptide Synthesis, 2nd rev. ed.; Springer-Verlag: Berlin, Heidelberg, New York, 1994; p 96.
24. The presence of valine at position 10 was verified by degradation of the formed DHFR with Glu-C endopeptidase, affording a peptide that encompassed amino acids 1-17. This peptide was identical with an authentic standard prepared by chemical synthesis.
25. Also supporting this interpretation was the lack of any degradation observed when the iodine-treated tRNA was analyzed by polyacrylamide gel electrophoresis at pH 5.0.
26. Preliminary experiments with aspartic acid derivatives having protected side chain carboxylates suggests that substantially improved yields may be realized in this fashion. See also ref 4.