Peptide synthesis in aqueous solution. IV. Preparation and properties of [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate(Z-ODSP), [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate(Boc-ODSP) and [p-(9-fluorenylmethyloxycarbon

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概要

• 論文の詳細を見る

• In order to increase the applications of the water-soluble active ester method, water-soluble acylating reagents, [<I>p</I>-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, [<I>p</I>-(<I>t</I>-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate and [<I>p</I>-(9-fluorenylmethyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, were synthesized from of <I>p</I>-hydroxyphenyldimethylsulfonium methyl sulfate. These compounds had high solubility (more than 30%) in water and were found to act as excellent water-soluble acylating reagents for the synthesis of <I>N</I>-benzyloxycarbonyl, <I>N</I>-<I>t</I>-butoxycarbonyl, <I>N</I>-9-fluorenylmethyloxycarbonyl amino acid derivatives in aqueous solution. They converted dipeptides to <I>N</I>-acyl-dipeptides in aqueous media as well as amino acids. In addition, they were found to be efficient reagents for protecting the side chains of lysine, ornithine, and cysteine.

• 公益社団法人 日本化学会の論文

著者

• Okai Hideo

  Department Of Fermentation Technology Faculty Of Engineering Hiroshima University

• KINOMURA Keisuke

  Department of Fermentation Technology, Faculty of Engineering, Hiroshima University

• Tamura Masahiro

  Department Of Fermentation Technology Faculty Of Engineering Hiroshima University

• KOUGE Katsushige

  Department of Fermentation Technology, Faculty of Engineering, Hiroshima University

• Azuse Ikunori

  Department Of Fermentation Technology Faculty Of Engineering Hiroshima University

• Hamatsu Fumio

  Sanshin Chemical Industrial Co. Ltd.

• Koizumi Tatsuya

  Sanshin Chemical Industrial Co. Ltd.

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