Hydrolytic Cleavage of Pyroglutamyl-peptide Bond. V. Selective Removal of Pyroglutamic Acid from Biologically Active Pyroglutamylpeptides in High Concentrations of Aqueous Methanesulfonic Acid

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概要

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• Application of aqueous methanesulfonic acid (MSA) for selective chemical removal of pyroglutamic acid (pGlu) residue from five biologically active pyroglutamyl-peptides (pGlu-X-peptides, X=amino acid residue at position 2) was examined. Gonadotropin releasing hormone (Gn-RH), dog neuromedin U-8 (d-NMU-8), physalaemin (PH), a bradykinin potentiating peptide (BPP-5a) and neurotensin (NT) as pGlu-X-peptides were incubated in either 70% or 90% aqueous MSA at 25℃. HPLC analysis of the incubation solutions showed that the main decomposition product was H-X-peptide derived from each pGlu-X-peptide by the removal of pGlu. The results revealed that the pGlu-X peptide bond had higher susceptibility than various internal amide bonds in the five peptides examined, including the Trp-Ser bond in Gn-RH, the C-terminal Asn-NH_2 in d-NMU-8, and the Asp-Pro bond in PH, whose acid susceptibility is well known. Thus, mild hydrolysis with high concentrations of aqueous MSA may be applicable to chemically selective removal of pGlu from pGlu-X-peptides for structural examinations.

• 社団法人日本薬学会の論文
• 2006-06-01

著者

• OHKI Kazuhiro

  Faculty of Pharmaceutical Sciences, Hokuriku University

• OKIMURA Keiko

  Faculty of Pharmaceutical Sciences, Hokuriku University

• SAKURA Naoki

  Faculty of Pharmaceutical Sciences, Hokuriku University

• HASHIMOTO Tadashi

  Faculty of Pharmaceutical Sciences, Hokuriku University

• Hashimoto T

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 橋本 忠

  北陸大・薬

• Ohnishi Kuniharu

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Ohnishi Kuniharu

  北陸大学 薬学部

• Ohki K

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Ohki Kazuhiro

  北陸大学 薬学部

• Ohki Kazuhiro

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Okimura K

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Okimura Keiko

  北陸大学 薬学部

• Okimura Keiko

  Faculty Of Pharmaceutical Sciences Hokuriku University

• 佐倉 直樹

  北陸大・薬

• Sakura N

  Hokuriku Univ. Kanazawa Jpn

• Sakura Naoki

  北陸大学 薬 生物活性

• Sakura Naoki

  北陸大学 薬学部

• Sakura Naoki

  Faculty Of Pharmaceutical Sciences Hokuriku University

• KOBAYASHI Junko

  Faculty of Pharmaceutical Sciences, Hokuriku University

• 橋本 忠

  北陸大学薬学部

• Kobayashi Junko

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Hashimoto Tadashi

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Hashimoto T

  Hokuriku Univ. Kanazawa Jpn

• Hashimoto Toshihiro

  Fac. Of Pharmaceutical Sciences Tokushima Bunri Univ.

• Hashimoto Tadashi

  Drug Metabolism Laboratories Drug Development Division Yamanouchi Pharmaceutical Co. Ltd.

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