Facile Solid-Phase Synthesis of Sulfated Tyrosine-Containing Peptides : Part II. Total Synthesis of Human Big Gastrin-II and Its C-Terminal Glycine-Extended Peptide(G34-Gly Sulfate)by the Solid-Phase Segment Condensation Approach^<1, 2)>
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概要
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Application of the fluoren-9-ylmethoxycarbonyl(Fmoc)-based solid-phase segment condensation appraoch to the preparation of sulfated peptides was investigated through the synthesis of human big gastrin-II, a 34-residue sulfated tryosine [Tyr(SO_3H)]-containing peptide. Highly acid-sensitive 2-chlorotrityl resin(Clt resin)was exclusively employed as an anchor-resin for the preparation of the peptide segments having the C-ter-minal Pro residue as well as of the Try(SO_3H)-containing resin-bound segment. By using the PyBOP-mediated coupling protocol [PyBOP=benzotriazolyloxytris(pryrrolidino)phosphonium hexafluorophoshate], we successively condensed each segment and constructed the 34-residue peptide-resin without any difficulty. The final acid treatment of the fully protected peptide-resin at low temperature(90% aqueous TFA, 0℃ for 8h), which can detach a Tyr(SO_3H)-containing peptide from the resin and remove the protecting groups concurrently with minimum deterioration of the sulfate, afforded a crude sulfated peptide. After one-step HPLC purification, a highly homogeneous human big gastrin-II was easily obtained in 14% yield from the protected peptide-resin. The sulfate from of the C-terminal glycine-extended gastrin(G34-Gly sulfate), a posttranslational processing intermediate of gastrin-II, was also successfully prepared with the segment condensation approach(11% yield). These results demonstrated the usefulness of the segment condensation protocol for preparing large Tyr(SO_3H)-containing peptides.
- 公益社団法人日本薬学会の論文
- 2001-08-01
著者
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FUTAKI Shiroh
Institute for Chemical Research, Kyoto University
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Fujiwara Hidetoshi
Niigata College Of Pharmacy
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Futaki Shiroh
Institute For Chemical Research Kyoto University
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Futaki S
Institute For Chemical Research Kyoto University
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Yagami T
National Inst. Health Sci. Tokyo Jpn
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Yagami Takeshi
National Institute Of Health Sciences
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Kitagawa K
Niigata College Of Pharmacy
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Kitagawa Kouki
Niigata College Of Pharmacy
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Fujiwara H
Niigata College Of Pharmacy
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AIDA Chikako
Niigata College of Pharmacy
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