PMID: 9176813Apr 1, 1997Paper

Comparative evaluation of the synthesis and purification of transmembrane peptide fragments. Rat bradykinin receptor fragment 64-97 as model

The Journal of Peptide Research : Official Journal of the American Peptide Society
E OliveiraM Tominaga

Abstract

The 34-residue peptide CTVAEIYLGNLAGADLILASGLPFWAITIANNFD (TM-34), corresponding to the 64-97 sequence of the rat bradykinin, receptor, was selected as a model of hydrophobic transmembrane peptide segment for systematic study of synthesis and purification strategies. Application of conventional Boc/Bzl chemistry resulted in very low yield of the synthesis (around 4%) when DMF was used as the solvent for coupling reactions. As shorter resin-bound fragments of TM-34 showed improved swelling in 80% NMP/DMSO, the synthesis was repeated in this mixed solvent and the yield increased to 12%. A comparative synthesis using optimized Fmoc chemistry and Fmoc-(FmocHmb) derivatives of Ala and Leu to prevent aggregation did not provide any detectable TM-34. Taken together, these results illustrate the synthetic problems associated with hydrophobic sequences, almost regardless of the chemistry used. As expected, the hydrophobicity of TM-34 and of most of its minor fragments made them scarcely soluble in common solvents. Purification could be achieved by loading the crude materials dissolved in 90% AcOH onto a C4 HPLC column and eluting with a TFA/MeCN linear gradient. CD studies of the TM-34 and of the shorter fragment with the 74-97 sequence...Continue Reading

References

Sep 1, 1992·International Journal of Peptide and Protein Research·J BedfordR C Sheppard
Sep 1, 1991·Proceedings of the National Academy of Sciences of the United States of America·A E McEachernK Jarnagin
Mar 1, 1990·International Journal of Peptide and Protein Research·G B Fields, R L Noble
Oct 1, 1988·Proceedings of the National Academy of Sciences of the United States of America·R F NuttI S Sigal
Jan 1, 1988·Annual Review of Biochemistry·S B Kent
Jan 12, 1983·Biochimica Et Biophysica Acta·C R NakaieA C Paiva

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Citations

May 30, 2006·Protein Science : a Publication of the Protein Society·Luciana MalavoltaClóvis R Nakaie
Dec 6, 2014·Organic & Biomolecular Chemistry·Yi-Chao HuangYi-Ming Li
Mar 21, 2020·Frontiers in Bioengineering and Biotechnology·Lena K MuellerAlesia A Tietze
Oct 16, 2010·The Journal of Organic Chemistry·Benoît BaptisteIvan Huc

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