Development of the ultimate third nucleobase required for expansion of the genetic code

2014 Fiscal Year Final Research Report

• Project/Area Number: 26560434
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Biomolecular chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: SEKINE Mitsuo 東京工業大学, 生命理工学研究科, 教授 (40111679)
• Project Period (FY): 2014-04-01 – 2015-03-31
• Keywords: 新規塩基対 / DNAポリメラーゼ / 人工塩基 / トリリン酸化 / 遺伝暗号拡張 / 光延反応

Outline of Final Research Achievements

In this study, the synthesis of dW, which was proposed as a new deoxynucleoside having a new synthetic nucleobase, was carried out. The reaction of diethyl 2-aminomalonate with ammonia gave the corresponding diamide for the synthesis of the nucleobase W. When the product was treated with triethyl orthoformate in isopropanol in the presence of formic acid, the key intermediate of 4-carbamoyl-5-hydroxyimidazole could be obtained in a high yield. For the synthesis of the final desired product, the Mitsunobu reaction using the O-triisopropylsilylated species of the imidazole derivative and 3’,5’-O-protected deoxyribose derivative is now studied.

Free Research Field

核酸有機化学