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Solid-Phase Synthesis Utilizing Azido-α-Amino Acids: Reduction of Azido-Protected Proline

  • Parissa Heshmati
  • James Whitehurst
  • Garland R. Marshall
Part of the American Peptide Symposia book series (APSY, volume 7)

Abstract

During an evaluation of azido-α-amino acids and their utility in solid-phase peptide chemistry, the octapeptide angiotensin II and a tripeptide thyrotropin-releasing hormone (TRH) analog have been prepared using Meldal’s procedure [1]. A necessary novel step was the reduction of the azido moiety of L-proline, a secondary amine constrained by a ring, to the corresponding free amine for coupling and peptide elongation. In this step a solution of tin(II)chloride (SnCl2), thiophenol (PhSH) and triethylamine (TEA) [2] in dimethylformamide (DMF) was added at ambient temperature to the azido-L-proline-peptide-resin to afford the desired free amino group (Figure 1) and make the use of azido- α-amino acids more general for solid-phase peptide synthesis.

Keywords

Acid Chloride Thionyl Chloride Free Amine Azido Group Blood Pressure Homeostasis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Meldal, M., Juliano, M.A., Jansson, A.M. Tetrahedron Lett. 38, 2531–2534 (1997).CrossRefGoogle Scholar
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    Bartra, M., Romea, P., Urpi, F., Vilarrasa, J. Tetrahedron 46, 587–594 (1990).CrossRefGoogle Scholar
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    Alper, P.B., Hung, S-C., Wong, C-H. Tetrahedron Lett. 37, 6029–6032 (1996).CrossRefGoogle Scholar
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    Lundquist, J.T., Pelletier, J.C. Org. Lett. 3, 781–783 (2001).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2001

Authors and Affiliations

  • Parissa Heshmati
    • 1
  • James Whitehurst
    • 1
  • Garland R. Marshall
    • 1
  1. 1.Department of Biochemistry and Molecular Biophysics, School of MedicineWashington UniversitySt. LouisUSA

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