Evaluation of the Trifluoromethanosulfonic Acid/Trifluoroacetic Acid/Thioanisole Cleavage Procedure for Application in Solid-Phase Peptide Synthesis

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概要

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• As an extension of our investigation of peptidyl-resin linkage stability towards different cleavage procedures used in the solid-phase peptide synthesis (SPPS) technique, the present paper evaluated the trifluoromethanesul-fonic acid (TFMSA)/trifluoroacetic acid (TFA)/thioanisole method, varying the type of resin (benzhydrylamineresin, BHAR; methylbenzhydrylamine-resin, MBHAR and 4-(oxymethyl)-phenylacetamidomethyl-resin, PAMR) and peptide resin-bound residue (Gly and Phe). The vasoactive angiotensin II (AII, DRVYIHPF) and its [Gly^8]-AII analogue linked to those resins used routinely in tert-butyloxycarbonyl (Boc)-SPPS chemistry were submitted comparatively to a time course study towards TFMSA/TFA cleavage. At 0°, [Gly^8]-AII was completely removed from all resins in less than 6h, but the hydrophobic Phe^8 moiety-containing AII sequence was only partially cleaved (not more than 15%) from BHAR or MBHAR in this period. At 25℃, [Gly^8]-AII cleavage time decreased to less than 2h irrespective of the solid support, and quantitative removal of AH from PAMR and MBHAR occurred in less than 3h. However, about 10-15h seemed to be necessary for cleavage of All from BHAR, and in this extended cleavage reaction a significant increase in peptide degradation rate was observed. Regardless of the cleavage temperature used, the decreasing order of acid stability measured for resins was BHAR>MBHAR>PAMR. Collectively, these findings demonstrated the feasibility of applying TFMSA/TFA solution as a substitute for anhydrous HF at the cleavage step in Boc-SPPS methodology. Care should be taken however, as the cleavage efficacy depends on multiple factors including the resin, peptide sequence, the time and temperature of reaction.

• 公益社団法人日本薬学会の論文
• 2001-09-01

著者

• OKADA Yoshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• MIRANDA ANTONIO

  Department of Biophysics, Escola Paulista de Medidna

• Miranda Antonio

  Department Of Biophysics Universidade Federal De Sao Paulo

• Okada Yoshio

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Miranda Antonio

  Department Of Biophysics Escola Paulista De Medidna

• JUBILUT Guita

  Department of Biophysics, Universidade Federal de Sao Paulo

• CILLI Eduardo

  Department of Biophysics, Universidade Federal de Sao Paulo

• TOMINAGA Mineko

  Department of Biophysics, Universidade Federal de Sao Paulo

• NAKAIE Clovis

  Department of Biophysics, Universidade Federal de Sao Paulo

• Jubilut Guita

  Department Of Biophysics Universidade Federal De Sao Paulo

• Okada Y

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Nakaie Clovis

  Department Of Biophysics Universidade Federal De Sao Paulo

• Cilli Eduardo

  Department Of Biophysics Universidade Federal De Sao Paulo

• Cilli Eduardo

  Department Of Biochemistry And Technological Chemistry Institute Of Chemistry Unesp

• Tominaga M

  Department Of Biophysics Universidade Federal De Sao Paulo

• Tominaga Mineko

  Department Of Biochemistry Institute Of Chemistry University Of Sao Paulo

• Ogino Y

  Teikyo Univ. School Of Medicine Chiba

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