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Title: 新規抗菌剤開発を指向したMraY阻害天然物ムライマイシン類の合成研究
Other Titles: Comprehensive Synthetic Study of Muraymycins toward the Development of Novel Antibacterial Agents
Authors: 谷野, 哲也1 Browse this author
市川, 聡2 Browse this author
魚谷, 幸一3 Browse this author
大山, 洋4 Browse this author
松田, 彰5 Browse this author
Authors(alt): TANINO, Tetsuya1
ICHIKAWA, Satoshi2
UOTANI, Koichi3
OYAMA, Hiroshi4
Keywords: muraymycin
Ugi four-component reaction
C-H amination reaction
Issue Date: Mar-2011
Publisher: 社団法人 日本薬学会
Volume: 131
Issue: 3
Start Page: 335
End Page: 346
Abstract:   This review describes the synthesis and structure-activity relationship (SAR) study of muraymycins (MRYs), which are potent antibacterial nucleoside antibiotics. The key elements of our synthetic approach include the preparation of L-epi-capreomycidine via a C-H amination reaction and a convergent assemblage to construct of the framework of MRYs using Ugi four component reaction. With this approach the first total synthesis of MRY D2 and its epimer, epi-MRY D2, which does not have lipophilic substituents, has been accomplished. The fact that MRY D2 and its epimer did not show any antibacterial activity indicated the lipophilic substituents of MRYs plays an important role in membrane-permeability. Hence, MRY analogues with lipophilic substituents were designed and synthesized simply by altering the aldehyde component in Ugi four-component assemblage. The MRY analogues with lipophilic substituents exhibited improved antibacterial activity against anti drug-resistant bacteria. It was also suggested that the accessory urea-dipeptide motif might contribute to MraY inhibitory and antibacterial activity. Our synthetic approach would effectively provide a variety of MRY analogues and resultant SAR information brings us directions to create further MRY analogues.
Type: article
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 松田 彰

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