Herein, we disclose an expedient visible-light-mediated, organophotoredox-catalyzed multicomponent synthesis of unnatural amino acids using a Katritzky salt, glyoxal derivatives, and substituted anilines. Mechanistically, an alkyl radical is generated from the Katritzky salt via a deaminative process that undergoes addition to the -generated imine to furnish α-amino acids in a moderate diastereoisomeric ratio. For the first time, we have demonstrated this deaminative protocol to access substituted β-amino acids from α-amino acid-derived Katritzky salts. Furthermore, α-amino amides are also generated from the corresponding 2-oxoacetamide derivatives.
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http://dx.doi.org/10.1021/acs.orglett.4c02152 | DOI Listing |
Proteoglycan Res
October 2024
Department of Biochemistry and Physiology, University of Oklahoma Health Sciences Center, Oklahoma City, Oklahoma, USA.
Hyaluronan (HA; [-3-GlcNAc-1-beta-4-GlcA-1-beta] ), an essential matrix polysaccharide of vertebrates and the molecular camouflage coating in certain pathogens, is polymerized by "HA synthase" (HAS) enzymes. Three HAS classes have been identified with biotechnological utility, but only the Class II PmHAS from Type A has been useful for preparation of very defined HA polymers in vitro. Two general chemoenzymatic strategies with different size products are possible: (1) repetitive step-wise extension reactions by sequential addition of a single monosaccharide from a donor UDP-sugar onto an acceptor (or "primer") comprised of a short glycosaminoglycan chain (e.
View Article and Find Full Text PDFBioorg Med Chem
December 2024
Jiangsu Provincial Key Laboratory of Drug Metabolism and Pharmacokinetics, State Key Laboratory of Natural Medicines, China Pharmaceutical University, Tongjiaxiang No. 24, Nanjing 210009, Jiangsu, China. Electronic address:
Recent advancements in Genetic Code Expansion (GCE) have significantly enhanced our understanding of post-translational modifications (PTMs), which are critical for protein regulation. GCE facilitates the precise incorporation of unnatural amino acids (UAAs) at specific sites within proteins of interest (POIs), making it a powerful tool for modulating PTMs in vivo. This review summarizes the various UAAs utilized to directly incorporate PTMs into proteins through GCE, with a focus on their applications in both histone and non-histone PTMs research.
View Article and Find Full Text PDFToxins (Basel)
December 2024
Research Department for Limnology, University of Innsbruck, Mondseestrasse 9, 5310 Mondsee, Austria.
Recently, the use of click chemistry for localization of chemically modified cyanopeptides has been introduced, i.e., taking advantage of promiscuous adenylation (A) domains in non-ribosomal peptide synthesis (NRPS), allowing for the incorporation of clickable non-natural amino acids (non-AAs) into their peptide products.
View Article and Find Full Text PDFSheng Wu Gong Cheng Xue Bao
December 2024
College of Animal Science and Technology, Northeast Agricultural University, Harbin 150030, Heilongjiang, China.
Antimicrobial peptides (AMPs) are small molecular peptides widely existing in the innate immunity of organisms, serving as the first line of defense. Natural AMPs possess various biological activities and are difficult to develop drug resistance. However, they are easily broken down by digestive enzymes in the body.
View Article and Find Full Text PDFBioorg Chem
December 2024
School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023, China. Electronic address:
Unnatural chemically modified nucleotide sugars UDP-4-SH-GalNAc was synthesized for the first time from a previously reported Benzyl 2-Amino-glucoypranoside derivative, with a total yield of 18.6%. UDP-4-SH-GalNAc was smaller in size than UDP-GalNAc calculated by Multiwfn, and its binding capability with glycosyltransferase was stronger than that of UDP-GalNAc and glycosyltransferase, which means the unnatural nucleotide sugars is equally well recognized by the enzyme and doped into the sugar chains.
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