Biocompatible Photoinduced Alkylation of Dehydroalanine for the synthesis of unnatural α-amino acids

JAC Delgado, JTM Correia, EF Pissinati… - Organic …, 2021 - ACS Publications
A site-selective alkylation of dehydroalanine to access protected unnatural amino acids is
described. The protocol is characterized by the wide nature of alkyl radicals employed, mild …

[HTML][HTML] A practical and scalable system for heteroaryl amino acid synthesis

RA Aycock, DB Vogt, NT Jui - Chemical Science, 2017 - pubs.rsc.org
A robust system for the preparation of β-heteroaryl α-amino acid derivatives has been
developed using photoredox catalysis. This system operates via regiospecific activation of …

Aminoalkyl radicals as powerful intermediates for the synthesis of unnatural amino acids and peptides

RA Aycock, CJ Pratt, NT Jui - ACS Catalysis, 2018 - ACS Publications
A robust method for the direct addition of unactivated tertiary amines to dehydroalanine
(Dha) derivatives has been developed. This method, which is driven by a photoredox …

Derivatization of amino acids and peptides via photoredox-mediated conjugate addition

O Zhang, JW Schubert - The Journal of Organic Chemistry, 2020 - ACS Publications
Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the
development of novel methods to increase the structural diversity of the unnatural amino …

Synthesis of Unnatural α‐Amino Acid Derivatives via Light‐Mediated Radical Decarboxylative Processes

K Merkens, FJ Aguilar Troyano… - Advanced Synthesis …, 2020 - Wiley Online Library
Unnatural amino acids (UAAs) are key building blocks with widespread application across
several scientific fields. Therefore, it is highly attractive to develop straightforward and simple …

Access to deuterated unnatural α-amino acids and peptides by photochemical acyl radical addition

L Liu, Z Deng, K Xu, P Jiang, H Du, J Tan - Organic Letters, 2021 - ACS Publications
A visible-light-enabled, photocatalyst-free conjugate addition reaction of dehydroamino
acids is disclosed. Employing 4-acyl-1, 4-dihydropyridines as both a radical reservoir and …

[HTML][HTML] Visible-light photoredox synthesis of unnatural chiral α-amino acids

M Jiang, Y Jin, H Yang, H Fu - Scientific reports, 2016 - nature.com
Unnatural chiral α-amino acids are widely used in fields of organic chemistry, biochemistry
and medicinal chemistry, and their synthesis has attracted extensive attention. Although the …

Synthesis of unnatural α-amino acids via photoinduced decatungstate-catalyzed Giese reactions of aldehydes

X Wang, Y Chen, H Song, Y Liu, Q Wang - Organic Letters, 2021 - ACS Publications
Synthesis of unnatural amino acids has long been a focus of chemistry research. Here, we
present an efficient, general method that furnishes γ-carbonyl α-amino acids via …

Photoinduced C(sp3)–H Functionalization of Glycine Derivatives: Preparation of Unnatural α-Amino Acids and Late-Stage Modification of Peptides

C Wang, R Qi, R Wang, Z Xu - Accounts of Chemical Research, 2023 - ACS Publications
Conspectus Peptides are essential components of living systems and contribute to critical
biological processes, such as cell proliferation, immune defense, tumor formation, and …

Access to unnatural α-amino acids via visible-light-mediated decarboxylative conjugate addition to dehydroalanine

AA Shah, MJ Kelly III, JJ Perkins - Organic letters, 2020 - ACS Publications
An expedient synthesis of β-alkyl α-amino acids is reported via application of
decarboxylative photocatalysis. The method utilizes abundant, diverse, and inexpensive …