van der Heden van Noort et al., 2011 - Google Patents

Ribosylation of adenosine: an orthogonally protected building block for the synthesis of ADP-ribosyl oligomers

van der Heden van Noort et al., 2011

Document ID
16785875145843506690
Author
van der Heden van Noort G
Overkleeft H
van der Marel G
Filippov D
Publication year
Publication venue
Organic Letters

External Links

Snippet

A method to ribosylate adenosine on the 2′ hydroxyl function in an α-selective fashion and in good yield is presented. Protective groups chosen for the acceptor and donor used in this glycosylation not only direct α-selectivity but also allow the construction of a fully …
Continue reading at pubs.acs.org (other versions)

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12QMEASURING OR TESTING PROCESSES INVOLVING ENZYMES OR MICRO-ORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00Measuring or testing processes involving enzymes, nucleic acids or micro-organisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68Measuring or testing processes involving enzymes, nucleic acids or micro-organisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids

Similar Documents

Publication Publication Date Title
van der Heden van Noort et al. Ribosylation of adenosine: an orthogonally protected building block for the synthesis of ADP-ribosyl oligomers
Kistemaker et al. Stereoselective ribosylation of amino acids
Liu et al. Metabolically generated stable isotope-labeled deoxynucleoside code for tracing DNA N6-methyladenine in human cells
Bean et al. Formation of a β-pyrimidine nucleoside by a free pyrimidine base and ribose in a plausible prebiotic reaction
Thadke et al. Facile synthesis of β-and α-arabinofuranosides and application to cell wall motifs of M. tuberculosis
Hari et al. Synthesis and properties of 2′-O, 4′-C-ethyleneoxy bridged 5-methyluridine
van der Heden van Noort et al. Synthesis of mono-ADP-ribosylated oligopeptides using ribosylated amino acid building blocks
Moyle et al. Method for the synthesis of mono-ADP-ribose conjugated peptides
Wachowius et al. Probing essential nucleobase functional groups in aptamers and deoxyribozymes by nucleotide analogue interference mapping of DNA
Gore et al. Synthesis, gene silencing, and molecular modeling studies of 4′-C-aminomethyl-2′-O-methyl modified small interfering RNAs
Kumar et al. Synthesis and hybridization studies of 2 ‘-amino-α-L-LNA and tetracyclic “Locked LNA”
Roday et al. Inhibition of ricin A-chain with pyrrolidine mimics of the oxacarbenium ion transition state
Resendiz et al. Direct strand scission in double stranded RNA via a C5-pyrimidine radical
Sørensen et al. Synthesis of a Bicyclic Analogue of AZT Restricted in an Unusual O4 ‘-Endo Conformation
Barlow et al. Deamination and Dimroth Rearrangement of Deoxyadenosine− Styrene Oxide Adducts in DNA
Saladino et al. Mechanism of degradation of purine nucleosides by formamide. Implications for chemical DNA sequencing procedures
Nishizaki et al. Solution Structure of an RNA⊙ 2 ‘-O-Methylated RNA Hybrid Duplex Containing an RNA⊙ DNA Hybrid Segment at the Center
Barlow et al. Investigation of hydrolytic deamination of 1-(2-hydroxy-1-phenylethyl) adenosine
Jiang et al. Reconstructing the substrate for uracil DNA glycosylase: tracking the transmission of binding energy in catalysis
Kumar et al. Double-headed nucleotides with arabino configuration: Synthesis and hybridization properties
Kawahara et al. Unprecedented Mild Acid-Catalyzed Desilylation of the 2 ‘-O-tert-Butyldimethylsilyl Group from Chemically Synthesized Oligoribonucleotide Intermediates via Neighboring Group Participation of the Internucleotidic Phosphate Residue
Sharma et al. Chemoenzymatic synthesis of C-4′-Spiro-oxetanoribonucleosides
Misiura et al. Synthesis of nucleoside α-thiotriphosphates via an oxathiaphospholane approach
Rosemeyer et al. Oligonucleotides Incorporating 7-(Aminoalkynyl)-7-deaza-2 ‘-deoxyguanosines: Duplex Stability and Phosphodiester Hydrolysis by Exonucleases
Tarashima et al. First synthesis of fully modified 4′-selenoRNA and 2′-OMe-4′-selenoRNA based on the mechanistic considerations of an unexpected strand break