Photoredox‐Catalyzed Minisci‐Type Acylation of Heterocyclic C−H Bonds with Amino Acid‐Tethered Dihydropyridines

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-02-04 DOI:10.1002/adsc.202401394
Heesang Yang , Hyungjin Shin , Yeonhee Lee , Dabeen Lim , Na Yeon Kwon , Amitava Rakshit , Pargat Singh , Hyun Jin Kim , Kyeongwon Moon , In Su Kim
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Abstract

Conjugation of amino acids to bioactive molecules has emerged as a promising strategy for optimizing pharmacological profiles of lead candidates in drug discovery. This study describes a photocatalytic Minisci‐type transfer reaction of N‐acyl amino acids into various N‐heterocycles. Notably, this protocol enables direct conjugation of amino acids into heterocyclic C−H bonds, eliminating the need for prefunctionalized substrates. A diverse array of N‐heterocycles, amino acids, oligopeptides, and drugs were used to demonstrate the potential of the proposed approach. In addition, the importance of this approach is demonstrated through its application in the DNA‐encoded library chemistry. Various synthetic transformations and preliminary mechanistic investigations were also explored.
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光氧化催化与氨基酸系连二氢吡啶的杂环C-H键的迷你型酰化
氨基酸与生物活性分子的偶联已成为优化药物发现中主要候选药物的药理学特征的一种有前途的策略。本研究描述了一种光催化n -酰基氨基酸转化成各种n -杂环的迷你型转移反应。值得注意的是,该方案能够将氨基酸直接偶联到杂环C-H键上,从而消除了对预功能化底物的需要。多种n -杂环、氨基酸、寡肽和药物被用来证明该方法的潜力。此外,通过其在dna编码文库化学中的应用证明了这种方法的重要性。还探讨了各种综合转化和初步的机理研究。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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