Summary
A new, general approach to the synthesis of 2-thiohydantoins from protected α-amino acid derivatives is now available, which allows the synthesis of sensitive thiohydantoins. A solid phase development system (SPDS) has also been established to facilitate comprehensive studies of C-terminal chemistries. Peptides are attached via their amino groups, and may be detached to perform subsequent analyses. In this way, the fate of the peptide portion may be determined after exposure to various reaction conditions. Here we report the application of these tools in C-terminal sequencing studies using a new reagent benzoyl isothiocyanate (BITC). Coupling and cleavage chemistry are conveniently monitored in the SPDS. Reasonably efficient sequencing of a simple peptide is shown.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Schlack, P. und Kumpf, W. (1926) Hoppe-Seyler’s Z. Physiol. Chemie 154, 126–170.
Edman, P., and Henschen, A. (1975) in “Protein Sequence Determination”, Needleman, S.B. Ed., Springer-Verlag, 232-279.
Inglis, A.S., Wilshire, J.F.K., Casagranda, F. and Laslett, R.L. (1989) in “Proceedings of the Seventh International Conference on Methods in Protein Sequence Analysis”, ed. B. Wittmann-Liebold, Springer-Verlag, 164-167.
Stark, G.R. (1972) in “Methods in Enzymology” (Hirs, C.H.W., and Timasheff, S.N., Eds.), Academic Press, N.Y. 25, 369.
Kenner, G.W., Khorana, H.G., and Stedman, R.J. (1953), J. Chem Soc. 673-678.
Meuth, J.L., Harris, D.E., Dwulet, F.E., Crowl-Powers, M.L., and Gurd, F.R.N. (1982) Biochemistry 21, 3750.
Bergmann, M. and Zervas, L.(1936) J. Biol. Chem. 113., 341.
Parham, M.E. and Loudon, G.M. (1978) Biochem. Biophys. Res. Commun., 80, 1–6.
Bailey, J.L. (1955) Biochem J. 60, 173.
Khorana, H.G. (1952) J. Chem. Soc. 2083-2088.
Tarr, G.E. (1975) in “Solid-Phase Methods in Protein Sequence Analysis” (R.A. Laursen, ed.), Pierce Chemical Co., Rockford IL, 139.
Previero, A., and Coletti-Previero, M-A. (1977) in “Solid Phase Methods in Protein Sequence Analysis”, INSERM Symposium #5, Eds. Previero and Coletti-Previero, Elsevier/North-Holland Biomed. Press, 49-56.
Rangarajan, M., (1988) in “Protein/Peptide Sequence Analysis: Current Methodologies” (Bhown, A.S., Ed.), CRC Press, Boca Raton, FL., 135–144.
Yamashita, S. (1971) Biochim. Biophys. Acta 229, 301.
Bailey, J.M. and Shively, J.E. (1990) Biochemistry 29, 3145–56.
Hawke, D.H., Lahm, H.-W., Shively, J.E. and Todd, C.W. (1987) Anal. Biochem., 166, 298.
Miller, C.G. and Shively, J.E. (1989) Abstract T188, The Third Symposium of the Protein Society, 29 Jul–2 Aug 1989, Seattle, WA.
Boyd, V.L., Hawke, D.H. and Geiser, T.G. (1990) Tetrahedron Letters, 21, 3849–52.
Woodward, R.B. and Olafson, R.A. (1986) Tetrahedron, Suppl. 7, 415–440.
Waley, S.G. and Watson, J.J. (1951), J. Chem. Soc. 2394.
Miller, C.G., Kong, C. and Shively, J.E. (1989) in “Techniques in Protein Chemistry”, T.E. Hugli, ed., Academic Press, San Diego, 67–78.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1991 Springer Basel AG
About this chapter
Cite this chapter
Hawke, D.H., Boyd, V.L. (1991). Chemical C-Terminal Sequencing. In: Jörnvall, H., Höög, JO., Gustavsson, AM. (eds) Methods in Protein Sequence Analysis. Advances in Life Sciences. Birkhäuser, Basel. https://doi.org/10.1007/978-3-0348-5678-2_3
Download citation
DOI: https://doi.org/10.1007/978-3-0348-5678-2_3
Publisher Name: Birkhäuser, Basel
Print ISBN: 978-3-0348-5680-5
Online ISBN: 978-3-0348-5678-2
eBook Packages: Springer Book Archive