One of the most popular one-pot glycosylation strategies is orthogonal one-pot synthesis, which was mainly based on thioglycosides. Despite its successful application, shortcomings of thioglycosides including aglycon transfers, interference of departing species and unpleasant odor restrict its application scope. Herein, we report a new and efficient orthogonal one-pot synthesis of oligosaccahrides based on glycosyl ortho-alkynylbenzoate, which solves the issues of thioglycoside-based orthogonal one-pot synthesis. Over a dozen of oligosaccharides have been efficiently synthesized by this method.
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http://dx.doi.org/10.1021/acs.orglett.9b00617 | DOI Listing |
ACS Sens
December 2024
Department of Chemistry, Faculty of Science, McGill University, Montreal, Quebec H3A 0B8, Canada.
We present a straightforward design approach to develop DNA-based light-up aptasensors. We performed the first systematic comparison of DNA fluorescent light-up aptamers (FLAPs), revealing key differences in affinity and specificity for their target dyes. Based on our analysis, two light-up aptamers emerged with remarkable specificity, fluorescence enhancement, and functionality in diverse environments.
View Article and Find Full Text PDFPolym Chem
May 2024
Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115, United States.
Glycopolymers have been employed as biomimetic glycoconjugates in both biological and biomedical research and applications. Among them, chain-end functionalized glycopolymers are very often explored for protein modification, microarray, biosensor, bioprobe and other applications. Herein, we report a straightforward synthesis of α,ω-end orthogonally functionalizable glycopolymers.
View Article and Find Full Text PDFChem Sci
December 2024
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University Wuhan Hubei 430072 China
Developing methodologies for the expedient construction of biologically important δ-valerolactones bearing a privileged azaarene moiety and a sterically congested all-carbon quaternary stereocenter is important and full of challenges. We present herein a novel multicatalytic strategy for the stereodivergent synthesis of highly functionalized chiral δ-valerolactones bearing 1,4-nonadjacent quaternary/tertiary stereocenters by orthogonally merging borrowing hydrogen and Michael addition between α-azaaryl acetates and allylic alcohols followed by lactonization in a one-pot manner. Enabled by Cu/Ru relay catalysis, this cascade protocol offers the advantages of atom/step economy, redox-neutrality, mild reaction conditions, and broad substrate tolerance.
View Article and Find Full Text PDFNon-standard amino acids (nsAAs) that are L-phenylalanine derivatives with aryl ring functionalization have long been harnessed in natural product synthesis, therapeutic peptide synthesis, and diverse applications of genetic code expansion. Yet, to date these chiral molecules have often been the products of poorly enantioselective and environmentally harsh organic synthesis routes. Here, we reveal the broad specificity of multiple natural pyridoxal 5'-phosphate (PLP)-dependent enzymes, specifically an L-threonine transaldolase, a phenylserine dehydratase, and an aminotransferase, towards substrates that contain aryl side chains with diverse substitutions.
View Article and Find Full Text PDFACS Omega
November 2024
Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy.
Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both β-1,4-d-Gulo and α-1,4-d-Manno oligosaccharides.
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