Synthesis of bombyxin-IV, an insulin superfamily peptide from the silkworm, Bombyx mori, by stepwise and selective formation of three disulfide bridges. |
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Authors: | Kazunori Maruyama Kouji Nagata Minoru Tanaka Hiromichi Nagasawa Akira Isogai Hironori Ishizaki Akinori Suzuki |
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Affiliation: | (1) Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo, Bunkyo-ku, 113 Tokyo, Japan;(2) Department of Biology, School of Science, Nagoya University, Chikusa-ku, 464-01 Nagoya, Japan |
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Abstract: | We report the synthesis of bombyxin-IV, a disulfide-linked, heterodimeric, insulin superfamily peptide from the silkworm,Bombyx mori. The two chains (A- and B-chains) were synthesized separately by the solid-phase method using fluoren-9-ylmethoxycarbonyl (Fmoc) group as a protecting group for -amino group. Three disulfide bonds were bridged step by step (A6–A11, A20–B22, and A7–B10) in a good yield. Synthetic bombyxin-IV was identical with natural one with regard to the retention time on a reversed-phase column and the molecular weight measured by mass spectrometry. Circular dichroism (CD) spectrum of the synthetic bombyxin-IV was very similar to that of the natural one. The specific activity of synthetic bombyxin-IV is equal to that of natural one (0.1 ng/Samia unit). These results suggest that the synthetic bombyxin-IV has the tertiary structure identical with the natural peptide. Our method developed for synthesis of bombyxin-IV would be generally applicable to the synthesis of insulin-like heterodimeric peptides. |
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Keywords: | Prothoracicotropic hormone insect neuropeptide insulin superfamily peptide synthesis selective formation of disulfide bridges |
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