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Development for Peptidomimetic Chemistry based on Chloroalkene Structures
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- Tamamura Hirokazu
- Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University
Bibliographic Information
- Other Title
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- クロロアルケン骨格を基盤としたペプチドミメティック化学への展開
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Description
<p>In drug discovery, various biologically active peptides have been discovered, characterized and modified for medicinal chemistry. However, the utilization of peptides as therapeutics has some limitation owing to several factors, including low metabolic stability towards proteolysis and undesired interactions with multiple receptors. Hence, the development of “peptidomimetc”, in which a part or whole of a molecule is modified, is an important strategy with which to enhance the stability or bioactivity of peptide-based drugs. In this situation, we have designed and developed a synthetic method for chloroalkene dipeptide isosteres (CADIs), which involves replacement of an amide bond in peptides with a chloroalkene structure, toward the peptidomimetc. By a developed synthetic method, an N-tert-butylsulfonyl protected CADI was obtained utilizing diastereoselective allylic alkylation with organocopper reagents as a key reaction. This CADI was also transformed into an N-Fmoc protected CADI in a few steps. In addition, The CADI could be used in Fmoc-based solid-phase peptide synthesis and applied to introduce for a bioactive peptide.</p>
Journal
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- Journal of Synthetic Organic Chemistry, Japan
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Journal of Synthetic Organic Chemistry, Japan 77 (9), 904-911, 2019-09-01
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
- 1390001277348436736
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- NII Article ID
- 130007705928
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- ISSN
- 18836526
- 00379980
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- Text Lang
- ja
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- Article Type
- journal article
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- KAKEN
- OpenAIRE
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- Abstract License Flag
- Disallowed