Synthesis, Three-dimensional Structure and Biological Activity of Glycosylated Calcitonin
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- Toma Kazunori
- The Noguchi Institute
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- Haneda Katsuji
- 神奈川工科大学応用化学科
Bibliographic Information
- Other Title
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- 糖鎖付加カルシトニンの合成,立体構造,生理活性
- トウサ フカ カルシトニン ノ ゴウセイ リッタイ コウゾウ セイリ カッセイ
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Abstract
More than 40 glycosylated calcitonin derivatives were synthesized using chemo-enzymatic procedure. The derivatives vary in the glycosylation site on calcitonin and/or the carbohydrate structure. For N-glycosylation with natural large oligosaccharide structures, transglycosylation reactions of endoglycosidases were employed. The yield of the transglycosylation reaction was improved and it became possible to prepare glycopeptides with two different natural carbohydrate structures on a single peptide. Using these derivatives, the effects of glycosylation on the peptide backbone conformation and the biological activity of calcitonin were studied. Some of the glycosylated calcitonin changed their backbone conformation depending mainly on the glycosylation site. The change in the hypocalcemic activity, the main biological activity of calcitonin, changed depending not only on the glycosylation site but also on the carbohydrate structure. The main cause of the carbohydrate structure-dependent change in the hypocalcemic activity was shown to be the altered biodistribution which was regulated by the carbohydrate structure.
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 63 (10), 995-1003, 2005
The Society of Synthetic Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390001205311295104
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- NII Article ID
- 130000928677
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- NII Book ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL BIB ID
- 7692674
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- Text Lang
- ja
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed