Development of Amide Condensation Catalysis Directed towards Peptide Synthesis

2015 Fiscal Year Final Research Report

• Project/Area Number: 26620079
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Nagoya University
• Principal Investigator: Ishihara Kazuaki 名古屋大学, 工学(系)研究科(研究院), 教授 (40221759)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: アミド縮合 / ボロン酸 / DMAPO / カルボン酸 / 脱水縮合 / 触媒 / 不飽和カルボン酸 / 協奏触媒

Outline of Final Research Achievements

In 1996, Ishihara et al. reported boronic acid-catalyzed dehydrative condensation between carboxylic acids and amines. Nevertheless, more excellent catalytic systems have been demanded for practical synthesis of amides and peptides. In this subject, we found that dehydrative condensation between carboxylic acids and amines more rapidly proceeded in the presence of catalytic amounts of boronic acid and N,N-dimethylaminopyridine N-oxide (DMAPO). After arboxylic acids were activated with boronic acids as mixed anhydrides, they were further activated with DMAPO as DMAPO esters. The latter intermediate was more active than the former one. Very interestingly, this new catalytic system, boronic acid/DMAPO, was effective for chemoselective amide condensation of conjugated carboxylic acids. In contrast, DMAP was much less effective than DMAPO.

Free Research Field

有機合成化学