DOI QR코드

DOI QR Code

Application of BMPI / HOBT Reagent in Solid-Phase Peptide Synthesis

  • Hong Nam Joo (Department of Applied Microbiology, College of Agriculture, Yeungnam University) ;
  • Choi Soo Kwan (Department of Chemistry, Korea University) ;
  • Koock Soon Uoong (Department of Chemistry, Korea University)
  • Published : 19890200

Abstract

The suitability of BMPI (2-bromo-N-methyl pyridinium iodide) for solid-phase peptide synthesis was investigated. The coupling rate of BMPI/HOBT procedure. BMPI/HOBT was superior to DCC/HOBT couplings using the solid-phase peptide bond formation proceeded to a greater degree of completion than DCC/HOBT method did. Double couplings with 2 equiv. of Bocamino acids and 1.5 equiv. of BMPI and $NEt_3$ and 2 equiv. of HOBT in DMF/MC (1:1 v/v) gave the best result for the preparation of a model compound. Stepwise solid phase peptide synthesis using BMPI/HOBT procedure was successfully utilized for the preparation of $(D-Ala)^2$-dynorphine A. BMPI/HOBT procedure for the synthesis of $(D-Ala)^2$-dynorphine gave better yield (20%) than DCC/HOBT procedure did.

Keywords

References

  1. J. Amer. Chem. Soc. v.77 J. C. Sheehan;G. P. Hess
  2. Principles of Peptide Synthesis M. Bodanszky
  3. The Peptides v.2 G. Barany;R. B. Merrifield;E. Gross(ed.);J. Meienhofer(ed.)
  4. Int. J. Peptide Protein Res. v.31 A. Fournier;C. T. Wang;A. M. Felix
  5. Tetrahedron v.36 P. rivaille;J. P. Gautron;B. Castro;G. Milhaud
  6. FEBS Lett. v.200 M. P. Audosset-Puech;M. Dufour;A. Kervan;J. Martine
  7. Chem. Lett. T. Mukaiyama;K. Saigo
  8. Chem. Lett. H. Huang;N. Iwasawa;T. Mukaiyama
  9. Justus Liebigs Ann. Chem. v.702 E. Schnabel
  10. Master Thesis, Korea University Synthesis of Dynorphine A analog with the new coupling reagent, BMPI S. K. Choi
  11. Korean Biochem. J. v.18 S. U. Koock;N. J. Hong;S. D. Shin
  12. J. Biol. Chem. v.200 W. Troll;R. K. Cannan
  13. Solid Phase Peptide Synthesis(2nd ed.) J. D. Young;J. M. Stewart
  14. The Peptieds v.1 E. Gross;J. Meienhofer

Cited by

  1. ChemInform Abstract: Application of BMPI/HOBT Reagent in Solid‐Phase Peptide Synthesis. vol.20, pp.31, 1989, https://doi.org/10.1002/chin.198931278