Abstract
Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.
Highlights
Amino acids (AAs) are an important class of compounds containing amino groups and carboxyl groups at the same time and fundamental building blocks of proteins responsible for life activities [1,2]
Different from the basic and common proteinogenic amino acids (PAAs), which can be found in proteins and have standard genetic codes, non-proteinogenic amino acids (NPAAs) are not naturally encoded, but essential building blocks, because do they take part in the composition of peptides and proteins with versatile functions [3,4], they act as multifunctional molecules, such as drugs (Figure 1a) [5], biotechnological tools (Figure 1b) [6], and catalysts (Figure 1c) [7]
For the other low active reaction sites, especially the abundant but inert C–H bonds of the PAAs, direct C–H functionalization in modern chemistry has emerged as a powerful way to synthesize versatile NPAAs directly and rapidly [17,18]
Summary
Amino acids (AAs) are an important class of compounds containing amino groups and carboxyl groups at the same time and fundamental building blocks of proteins responsible for life activities [1,2]. For the other low active reaction sites, especially the abundant but inert C–H bonds of the PAAs, direct C–H functionalization in modern chemistry has emerged as a powerful way to synthesize versatile NPAAs directly and rapidly [17,18]. The transition-metal-catalyzed C–H functionalization of PAAs has been well developed, the employment of expensive and polluting heavy. The transition-metal-catalyzed C–H functionalization of PAAs has been well developed, the employment of expensive and polluting heavy metal, the harsh reaction conditions metal,as thethe harsh reaction conditions such as high temperature limited practical application such high temperature limited itsthe practical application to a its certain extent. PAA derivatives directly toward NPAAs review, weinfocus our attention onC–H the recent advances inofthe photo-mediated.
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