Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C–H Functionalization

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.

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

“…Modifications of amino acids are fundamental transformations as they provide drugs, biotechnological tools, and catalysts. , A photocatalytic example in flow is the arylation of cysteine by Noël et al (Scheme ). , In this case, a diazonium salt was formed in situ starting from an aniline and t BuONO.…”

Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

“…Moreover, photo-mediated reactions to synthesize non-proteinogenic amino acids and peptides, including the glycosylated amino acids and peptides, exhibit high competence, broad functional group tolerance and great energy-saving performance. [96][97][98] Goddard-Borger's group has developed a photo-mediated Ni-catalyzed cross-coupling reaction of 4-bromophenylalanine 36 or 2-bromotryptophan derivatives 39 with commercially available mannosyl bromide 37 in 72-78 % yields (Scheme 7a). [99] Although tertiary amine could be used as terminal reductant and base in the Ni/photoredox dual catalysis, [100][101] poor result was obtained here when DIPEA was added only.…”

“…[107][108][109][110][111][112][113][114][115][116][117][118][119] Moreover, direct CÀ H activation of amino acids has been a powerful and promising strategy to synthesize versatile non-proteinogenic amino acids (NPAAs) and peptides directly and rapidly. [97,[120][121][122][123]…”

“…Since visible light has been considered as one of the most green and renewable energies, photocatalysis has become an appealing noncanonical synthetic method widely applied in redox, [91–92] cross‐coupling, [93–94] and C−H functionalization reactions, [95] for the mild reaction conditions, simple operation, as well as the employment of sustainable light source. Moreover, photo‐mediated reactions to synthesize non‐proteinogenic amino acids and peptides, including the glycosylated amino acids and peptides, exhibit high competence, broad functional group tolerance and great energy‐saving performance [96–98] …”

Effect Of Non-Protein Amino Acid (BABA) On Gastrointestinal Tissues Of Male Rats And Some Negative Enterobacteria

“…Non-proteinogenic amino acids (NPAAs) have attracted great interest for their fundamental applications in biology and chemistry (Yuan et al, 2020). It can be involved in the food chain.…”