A branched Man(5) oligosaccharide has been synthesized by sequential regioselective glycosylations on a mannose-tetraol with n-pentenyl orthoester glycosyl-donors promoted by NIS/BF(3)·Et(2)O, in CH(2)Cl(2). An extended n-pentenyl chain was incorporated into the tetraol acceptor to facilitate (a) the solubility of the starting tetraol in CH(2)Cl(2), and (b) future manipulations at the reducing end of the Man(5) oligosaccharide.
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http://dx.doi.org/10.1039/c2ob26432c | DOI Listing |
JACS Au
November 2024
School of Chemistry, Cantock's Close, University of Bristol, Bristol BS8 1TS, U.K.
A continuous microfluidic glycosylation strategy that requires no chromatography between steps and significantly expedites glycosylation chemistry is described. This practical approach incorporates the advantages of imidazolium-based chromatography-free purification and in situ mass spectrometry reaction monitoring to achieve fast reaction optimization and shorter reaction times. We demonstrate the utility of this strategy in the synthesis of a series of glycoside targets, including an α-(1,6)-trimannoside and a branched Man oligomannoside, within 1 day.
View Article and Find Full Text PDFMol Cancer Ther
May 2024
Basic Medicine Research and Innovation Center for Novel Target and Therapeutic Intervention, Ministry of Education, Institute of Life Sciences, the Second Affiliated Hospital of Chongqing Medical University, Chongqing Medical University, Chongqing, China.
Aberrant N-linked glycosylation is a prominent feature of cancers. Perturbance of oligosaccharide structure on cell surfaces directly affects key processes in tumor development and progression. In spite of the critical role played by N-linked glycans in tumor biology, the discovery of small molecules that specifically disturbs the N-linked glycans is still under investigation.
View Article and Find Full Text PDFChemistry
January 2024
Department of Organic Chemistry, Faculty of Chemistry, University of Seville, C/ Profesor García González 1, 41012, Sevilla, Spain.
The "carbohydrate chemical mimicry" exhibited by sp -iminosugars has been utilized to develop practical syntheses for analogs of the branched high-mannose-type oligosaccharides (HMOs) Man and Man . In these compounds, the terminal nonreducing Man residues have been substituted with 5,6-oxomethylidenemannonojirimycin (OMJ) motifs. The resulting oligomannoside hemimimetic accurately reproduce the structure, configuration, and conformational behavior of the original mannooligosaccharides, as confirmed by NMR and computational techniques.
View Article and Find Full Text PDFJ Inherit Metab Dis
July 2021
Division of Genetic Medicine, Department of Pediatrics, University of Washington School of Medicine, Seattle, Washington, USA.
J Biotechnol
October 2020
Max Planck Institute for Dynamics of Complex Technical Systems, Bioprocess Engineering, Sandtorstr. 1, 39106 Magdeburg, Germany; Otto-von-Guericke University Magdeburg, Chair of Bioprocess Engineering, Postfach 4120, 39106 Magdeburg, Germany. Electronic address:
A wide range of glycoproteins can be recombinantly expressed in aglycosylated forms in bacterial and cell-free production systems. To investigate the effect of glycosylation of these proteins on receptor binding, stability, efficacy as drugs, pharmacodynamics and pharmacokinetics, an efficient glycosylation platform is required. Here, we present a cell-free synthetic platform for the in vitro N-glycosylation of peptides mimicking the endoplasmic reticulum (ER) glycosylation machinery of eukaryotes.
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