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Thioester deprotection using a biomimetic NCL approach.
Front Chem
August 2022
Laboratorio de Química Farmacéutica (DQO), Facultad de Química, Universidad de la República, Montevideo, Uruguay.
The reversibility of the thiol-thioester linkage has been broadly employed in many fields of biochemistry (lipid synthesis) and chemistry (dynamic combinatorial chemistry and material science). When the transthioesterification is followed by a S-to-N acyl transfer to give an amide bond, it is called Native Chemical Ligation (NCL), a high-yield chemoselective process used for peptide synthesis. Recently, we described thioglycolic acid (TGA) as a useful reagent for thioester deprotection both in solution and anchored to a solid-support under mild conditions.
View Article and Find Full Text PDFOligonucleotides Containing 1-Aminomethyl or 1-Mercaptomethyl-2-deoxy-d-ribofuranoses: Synthesis, Purification, Characterization, and Conjugation with Fluorophores and Lipids.
Bioconjug Chem
February 2021
Department of Chemical and Biomolecular Nanotechnology, Institute for Advanced Chemistry of Catalonia (IQAC, CSIC), 08034-Barcelona, Spain.
Oligonucleotide conjugates are widely used as therapeutic drugs, gene analysis, and diagnostic tools. A critical step in the biologically relevant oligonucleotide conjugates is the design and synthesis of functional molecules that connect oligonucleotide with ligands. Here, we report the synthesis and application for oligonucleotide functionalization of novel tethers based on aminomethyl and mercaptomethyl sugar derivatives.
View Article and Find Full Text PDFRole of Metals and Thiolate Ligands in the Structures and Electronic Properties of Group 5 Bimetallic-Thiolate Complexes.
Inorg Chem
September 2020
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
Syntheses, structures, and electronic properties of group 5 metal-thiolate complexes that exhibit unusual coordination modes of thiolate ligands have been established. Room-temperature reaction of [Cp*VCl] (Cp* = η-CMe) with Na[B(SCHS)] led to the formation of [Cp*VO{(SCH)S}] (). The solid-state X-ray structure of shows the formation of six-membered l,3,5-trithia-2-vanadacyclohexane that adopted a chair conformation.
View Article and Find Full Text PDFAn Exceptionally Close, Non-Bonded Hydrogen-Hydrogen Contact with Strong Through-Space Spin-Spin Coupling.
Angew Chem Int Ed Engl
February 2018
Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.
Condensation of 1,8,13-tris(mercaptomethyl)triptycene and tris(bromomethyl)methane yields an in,in-cyclophane with two inwardly directed methine groups. Based on X-ray analysis and DFT and MP2 calculations, the hydrogen-hydrogen non-bonded contact distance is estimated to be 1.50-1.
View Article and Find Full Text PDFSynthesis and cellular studies of polyamine conjugates of a mercaptomethyl-carboranylporphyrin.
Bioorg Med Chem
January 2013
Louisiana State University, Department of Chemistry, Baton Rouge, LA 70803, USA.
Seven polyamine conjugates of a tri(p-carboranylmethylthio)tetrafluorophenylporphyrin were prepared in high yields by sequential substitution of the p-phenyl fluoride of tetrakis(pentafluorophenyl)porphyrin (TPPF), and investigated as boron delivery agents for boron neutron capture therapy (BNCT). The polyamines used were derivatives of the natural-occurring spermine with different lengths of the carbon chains, terminal primary amine groups and, in two of the conjugates, additional aminoethyl moieties. A tri(polyethylene glycol) conjugate was also synthesized for comparison purposes.
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