Environmentally Friendly Chemical Synthesis of Peptides Achieved by Slight Electron Transfer

2018 Fiscal Year Final Research Report

• Project/Area Number: 17K19222
• Research Category: Grant-in-Aid for Challenging Research (Exploratory)
• Allocation Type: Multi-year Fund
• Research Field: Agricultural chemistry and related fields
• Research Institution: Tokyo University of Agriculture and Technology
• Principal Investigator: Chiba Kazuhiro 東京農工大学, (連合)農学研究科(研究院), 教授 (20227325)
• Project Period (FY): 2017-06-30 – 2019-03-31
• Keywords: ペプチド合成 / 有機合成化学 / 電気化学 / 電解合成

Outline of Final Research Achievements

In this study, we developed a reaction that completes the formation of amide bond continuously by electrochemical treatment. As a result, electrolytic treatment of triphenylphosphine in dichloromethane revealed that various peptide syntheses were completed almost quantitatively. By combining the peptide synthesis with a highly hydrophobic tag in advance, the obtained product and unnecessary reagents can be easily separated, and furthermore, triphenylphosphine oxide which is a product after deoxygenation It was regenerated to triphenylphosphine by electrochemical reduction treatment. This result opens up the possibility as a new green chemistry which suppresses consumption of a large amount of dehydration condensation agent such as peptide by slight electron transfer.

Free Research Field

生物有機化学、有機合成化学、ペプチド化学

Academic Significance and Societal Importance of the Research Achievements

多段階の化学反応を要する化学物質生産において，反応毎の分離精製に関する工数の他，試薬や溶媒，廃棄物の総量を極限まで削減することは持続可能な社会構築の基盤となる重要な技術である．近年、次世代医薬として中分子化合物に注目が集まる中で、その中核をなるペプチド等の製造に必要となるアミド結合形成に関する革新技術の導入は重要である．現在，アミド結合形成を数十回繰り返す化学反応生産プロセスでは，アミド結合1つあたり1分子以上の縮合剤を消費し同時にその分解物が発生するという大きな課題がある．本研究成果は，廃棄物やエネルギー消費を大幅に削減する新たなアミド結合形成方法に関する提案として位置づけられるものである．