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High-yield and high-purity amide bond formation using DMTMM PF6 for DNA-encoded libraries
Takumi Hosozawa1, Masatoshi Niwa1, Hisayuki Takeuchi1
1Pharmaceutical Research Department, Chemical Research Laboratories, Nissan Chemical Corporation, 10-1, Tsuboi-Nishi 2-chome, Funabashi, Chiba, Japan.
Bioorganic & Medicinal Chemistry Letters
|July 2, 2024
Summary
DMTMM PF6 enhances DNA amidation reactions, achieving higher yields than other reagents, especially for difficult compounds. This improves DNA-encoded library synthesis and expands available chemical building blocks.
Area of Science:
- Chemical Synthesis
- Organic Chemistry
- Biotechnology
Background:
- Amidation reactions are crucial for synthesizing DNA-encoded libraries.
- Existing methods like HATU and DMTMM Cl have limitations with sterically hindered substrates.
- Efficient on-DNA amidation is key for expanding molecular diversity in libraries.
Purpose of the Study:
- To evaluate the efficacy of DMTMM PF6 for improving on-DNA amidation reactions.
- To compare the performance of DMTMM PF6 against HATU and DMTMM Cl.
- To demonstrate the utility of DMTMM PF6 for synthesizing high-purity DNA-encoded libraries.
Main Methods:
- On-DNA amidation reactions were performed using DMTMM PF6.
- Comparative analysis was conducted using HATU and DMTMM Cl as controls.
- Sterically hindered amines and carboxylic acids were employed as challenging substrates.
Main Results:
- DMTMM PF6 exhibited significantly higher conversion rates compared to HATU and DMTMM Cl.
- The reagent effectively facilitated amidation with sterically hindered building blocks.
- High-purity DNA-encoded libraries were synthesized efficiently using the developed method.
Conclusions:
- DMTMM PF6 is a superior reagent for on-DNA amidation, particularly for challenging substrates.
- This method expands the scope of building blocks usable in DNA-encoded library synthesis.
- The improved efficiency and purity facilitate the creation of more diverse and complex chemical libraries.
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