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Synthesis of glycol nucleic acids.

Synthesis of benzene‐glycol nucleic acids and their biophysical and biological properties.

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Solid‐phase synthesis of glyco‐oligonucleotide conjugates.

T1 - Synthesis and characterization of oligonucleotides containing 2′-fluorinated thymidine glycol as inhibitors of the endonuclease III reaction

Synthesis of two mirror image 4‐helix junctions derived from glycerol nucleic acid.

Pools of oligonucleotide conjugates consisting of 10-400 different molecular species were synthesized. The conjugates contained a varying number of ethylene glycol units attached to 3'-terminal, 5'-terminal and internal positions of the oligonucleotides. Conjugate synthesis was performed by phosphoramidite solid phase chemistry using suitably protected polyethylene glycol phosphoramidites and PEG-derivatized solid supports containing polydisperse PEGs of various molecular weight ranges. The pools were analyzed and fractionated by chromatographic and electrophoretic techniques, and the composition of isolated conjugates was revealed by matrix-assisted laser desorption/ionization mass spectrometry. The number and attachment sites of coupled ethylene glycol units greatly influence the hydrophobicity of the conjugates, as well as their electrophoretic mobilities. Conjugation had little effect on the hybridization behavior of oligonucleotide conjugates with unmodified complementary oligonucleotide strands. Melting temperatures were between 67 and 73 degrees C, depending on the size and number of coupled PEG chains, compared to 68 degrees C for the unmodified duplex. Conjugates with PEG coupled to both 3'- and 5'-terminal positions showed a more than 10-fold increase in exonuclease stability.

Oligonucleotide synthesis; Quantification of nucleic acids;

Automated incorporation of polyethylene glycol into synthetic oligonucleotides.

Endonuclease III is a base excision repair enzyme that recognizes oxidized pyrimidine bases including thymine glycol. This enzyme is a glycosylase/AP-lyase and forms a Schiff base-type intermediate with the substrate after the damaged base is removed. To investigate its substrate recognition mechanism by X-ray crystallography, we synthesized oligonucleotides containing 2'-fluorothymidine glycol (1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5,6-dihydro-5,6-dihydroxythymine), expecting that the electron-withdrawing fluorine atom at the 2' position would stabilize the covalent intermediate. Complex formation of the substrate analogs containing each thymine glycol isomer with endonuclease III was analyzed.

N2 - Endonuclease III is a base excision repair enzyme that recognizes oxidized pyrimidine bases including thymine glycol. This enzyme is a glycosylase/AP-lyase and forms a Schiff base-type intermediate with the substrate after the damaged base is removed. To investigate its substrate recognition mechanism by X-ray crystallography, we synthesized oligonucleotides containing 2'-fluorothymidine glycol (1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5,6-dihydro-5,6-dihydroxythymine), expecting that the electron-withdrawing fluorine atom at the 2' position would stabilize the covalent intermediate. Complex formation of the substrate analogs containing each thymine glycol isomer with endonuclease III was analyzed.

Synthesis of Glycerol Nucleic Acid (GNA) …

Synthesis and properties of oligodeoxyribonucleotide‐polyethylene glycol conjugates.

Quanta BioDesign is a research and manufacturing company committed to the development of a full range of discrete polyethylene glycol (dPEG®) PEGylation reagents for applications in diagnostics, therapeutics, peptide synthesis, oligonucleotide synthesis, and nanotechnology.

AB - Endonuclease III is a base excision repair enzyme that recognizes oxidized pyrimidine bases including thymine glycol. This enzyme is a glycosylase/AP-lyase and forms a Schiff base-type intermediate with the substrate after the damaged base is removed. To investigate its substrate recognition mechanism by X-ray crystallography, we synthesized oligonucleotides containing 2'-fluorothymidine glycol (1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5,6-dihydro-5,6-dihydroxythymine), expecting that the electron-withdrawing fluorine atom at the 2' position would stabilize the covalent intermediate. Complex formation of the substrate analogs containing each thymine glycol isomer with endonuclease III was analyzed.

T., Expedient Synthesis of Triazole-Linked Glycosyl Amino Acids and Peptides.
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  • DNA & RNA & ZNA Oligonucelotide Synthesis | …

    New solid support for the synthesis of 3′‐oligonucleotide conjugates through glyoxylic oxime bond formation.

  • Quanta BioDesign, dPEG®, dPEG, discrete PEG

    A convenient synthesis of oligonucleotides with a 3′‐phosphoglycolate and 3′‐phosphoglycaldehyde terminus.

  • Click Chemistry Publications - Scripps Research Institute

    Synthesis and properties of cholesteryl‐modified triple‐helix forming oligonucleotides containing a triglycyl linker.

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