BIOMAT Database Logo BIOMAT Database Logo

Glucose-derived 3'-(carboxymethyl)-3'-deoxyribonucleosides and 2', 3'-lactones as synthetic precursors for amide-linked oligonucleotide analogues. 2000

M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Department of Chemistry, Brigham Young University, Provo, Utah 84602-5700, USA.

Treatment of a 1,2-O-isopropylidene-3-ketopentofuranose derivative (obtained from D-glucose) with [(ethoxycarbonyl)methylene]triphenylphosphorane and catalytic hydrogenation of the resulting alkene gave stereodefined access to 3-(carboxymethyl)-3-deoxy-D-ribofuranose derivatives. Esters of 5-O-acetyl- or 5-azido-5-deoxy-3-(carboxymethyl)-D-ribofuranose were coupled with nucleobases to give branched-chain nucleoside derivatives. Ester saponification and protecting group manipulation provided 2'-O-(tert-butyldimethylsilyl) ethers of 5'-azido-5'-deoxy- or 5'-O-(dimethoxytrityl) derivatives of 3'-(carboxymethyl)-3'-deoxyribonucleosides that are effective precursors for synthesis of amide-linked oligoribonucleosides.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009841 Oligonucleotides Polymers made up of a few (2-20) nucleotides. In molecular genetics, they refer to a short sequence synthesized to match a region where a mutation is known to occur, and then used as a probe (OLIGONUCLEOTIDE PROBES). (Dorland, 28th ed) Oligonucleotide
D003839 Deoxyadenosines Adenosine molecules which can be substituted in any position, but are lacking one hydroxyl group in the ribose part of the molecule. Adenine Deoxyribonucleosides,Adenylyldeoxyribonucleosides,Deoxyadenosine Derivatives,Deoxyribonucleosides, Adenine,Derivatives, Deoxyadenosine
D005947 Glucose A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. Dextrose,Anhydrous Dextrose,D-Glucose,Glucose Monohydrate,Glucose, (DL)-Isomer,Glucose, (alpha-D)-Isomer,Glucose, (beta-D)-Isomer,D Glucose,Dextrose, Anhydrous,Monohydrate, Glucose
D013936 Thymidine A nucleoside in which THYMINE is linked to DEOXYRIBOSE. 2'-Deoxythymidine,Deoxythymidine,2' Deoxythymidine

Related Publications

M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Structural basis for the RNA binding selectivity of oligonucleotide analogues containing alkylsulfide internucleoside linkages and 2'-substituted 3'-deoxyribonucleosides.
October 1995, Nucleic acids research,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthetic analogues of polynucleotides. IX. Synthesis of 3'-O-carboxymethyl-2'-deoxyribonucleosides and their use in the synthesis of an analogue of 2'-deoxyadenylyl-(3' leads to 5'-)-thymidine 3'-phosphate.
January 1973, Journal of the Chemical Society. Perkin transactions 1,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
[Oligonucleotide analogues bearing an acyclonucleoside linked by an internucleotide amide bond].
January 2008, Bioorganicheskaia khimiia,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthesis of oligomers derived from amide-linked neuraminic acid analogues.
February 2004, The Journal of organic chemistry,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Preparation and properties of 2',5'-linked oligonucleotide analogues containing 3'-O,4'-C-methyleneribonucleosides.
February 1999, Bioorganic & medicinal chemistry letters,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthetic analogues of polynucleotides. X. The synthesis of poly-(3'-O-carboxymethyl-2'-deoxyadenosine) and its interaction with polynucleotides.
February 1973, Biochimica et biophysica acta,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
February 1987, Journal of medicinal chemistry,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors.
January 2023, Beilstein journal of organic chemistry,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
[Oligonucleotide analogues containing a C3'-NH-C(O)-CH(2)-C5' amide internucleotide bond].
January 2010, Bioorganicheskaia khimiia,
M J Robins, and B Doboszewski, and V A Timoshchuk, and M A Peterson
Synthetic analogues of polynucleotides. (Part) XIV. The synthesis of poly (3'-0-carboxymethyl-2'-deoxycytidine) and its interaction with polyinosinic acid.
May 1975, Nucleic acids research,
Copied contents to your clipboard!