ChemInform Abstract: Why Pentose and Not Hexose Nucleic Acids? Part 2. Preparation of Oligonucleotides Containing 2′,3′-Dideoxy-β-D-glucopyranosyl Building Blocks

ChemInform ◽  
2010 ◽  
Vol 23 (47) ◽  
pp. no-no
Author(s):  
M. BOEHRINGER ◽  
H.-J. ROTH ◽  
J. HUNZIKER ◽  
M. GOEBEL ◽  
R. KRISHNAN ◽  
...  
Keyword(s):  
Nucleic Acids ◽  
Building Blocks

scholarly journals Electronically Excited States of Potential Interstellar, Anionic Building Blocks for Astrobiological Nucleic Acids

2021 ◽  
Vol 8 ◽  
Author(s):  
Taylor J. Santaloci ◽  
Marie E. Strauss ◽  
Ryan C. Fortenberry
Keyword(s):  
Nucleic Acids ◽  
Excited States ◽  
Lone Pair ◽  
Building Blocks ◽  
Hydroxyl Group ◽  
Quantum Chemical Analysis ◽  
Electronically Excited States ◽  
Neutral Radical ◽  
Electronically Excited ◽  
Electron Withdrawing Group

Functionalizing deprotonated polycyclic aromatic hydrocarbon (PAH) anion derivatives gives rise to electronically excited states in the resulting anions. While functionalization with −OH and −C2H, done presently, does not result in the richness of electronically excited states as it does with −CN done previously, the presence of dipole-bound excited states and even some valence excited states are predicted in this quantum chemical analysis. Most notably, the more electron withdrawing −C2H group leads to valence excited states once the number of rings in the molecule reaches three. Dipole-bound excited states arise when the dipole moment of the corresponding neutral radical is large enough (likely around 2.0 D), and this is most pronounced when the hydrogen atom is removed from the functional group itself regardless of whether functionalized by a hydroxyl or enthynyl group. Deprotonatation of the hydroxyl group in the PAH creates a ketone with a delocalized highest occupied molecular orbital (HOMO) unlike deprotonation of a hydrogen on the ring where a localized lone pair on one of the carbon atoms serves as the HOMO. As a result, hydroxyl functionlization and subsequent deprotonation of PAHs creates molecules that begin to exhibit structures akin to nucleic acids. However, the electron withdrawing −C2H has more excited states than the electron donating −OH functionalized PAH. This implies that the −C2H electron withdrawing group can absorb a larger energy range of photons, which signifies an increasing likelihood of being stabilized in the harsh conditions of the interstellar medium.

Synthesis of new building blocks for peptide nucleic acids containing monomers with variations in the backbone

1997 ◽  
Vol 7 (6) ◽  
pp. 681-686 ◽  
Author(s):  
Stephan Jordan ◽  
Christoph Schwemler ◽  
Winfried Kosch ◽  
Axel Kretschmer ◽  
Eckhardt Schwenner ◽  
...  
Keyword(s):  
Nucleic Acids ◽  
Peptide Nucleic Acids ◽  
Building Blocks

Microwave Assisted Synthesis of N-(ethoxycarbonylmethyl)-nucleobases: Building Blocks for PNAs

2005 ◽  
Vol 2005 (3) ◽  
pp. 167-168 ◽  
Author(s):  
Gui-Rong Qu ◽  
Yong Li ◽  
Su-Hui Han
Keyword(s):  
Microwave Irradiation ◽  
Nucleic Acids ◽  
Peptide Nucleic Acids ◽  
Building Blocks ◽  
Microwave Assisted Synthesis ◽  
Ethyl Bromoacetate ◽  
Microwave Assisted

The synthesis of N1/N9- (Ethoxycarbonylmethyl)pyrimidine/purine using as synthons for peptide nucleic acids has been described. Microwave irradiation provided the desired products by alkylation of the appropriately protected natural and substituted nucleobases with ethyl bromoacetate within 4–7 min in 48–85% yields.

scholarly journals Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids

2013 ◽  
Vol 24 (5) ◽  
pp. 832-839 ◽  
Author(s):  
Xavier Elduque ◽  
Albert Sánchez ◽  
Kapil Sharma ◽  
Enrique Pedroso ◽  
Anna Grandas
Keyword(s):  
Nucleic Acids ◽  
Peptide Nucleic Acids ◽  
Building Blocks

Fmoc-Protected Altritol Phosphoramidite Building Blocks and Their Application in the Synthesis of Altritol Nucleic Acids (ANAs)

2007 ◽  
Vol 2007 (9) ◽  
pp. 1446-1456 ◽  
Author(s):  
Mikhail Abramov ◽  
Guy Schepers ◽  
Arthur Van Aerschot ◽  
Piet Herdewijn
Keyword(s):  
Nucleic Acids ◽  
Building Blocks

scholarly journals DNA Modified with Boron–Metal Cluster Complexes [M(C2B9H11)2]—Synthesis, Properties, and Applications

2018 ◽  
Vol 19 (11) ◽  
pp. 3501 ◽  
Author(s):  
Agnieszka Olejniczak ◽  
Barbara Nawrot ◽  
Zbigniew Leśnikowski
Keyword(s):  
Nucleic Acids ◽  
Metal Cluster ◽  
Building Blocks ◽  
Molecular Wires ◽  
Molecular Structures ◽  
Metal Centers ◽  
Cluster Complexes ◽  
Boron Cluster ◽  
Nucleic Acid Therapeutics ◽  
Synthesis Properties

Together with tremendous progress in biotechnology, nucleic acids, while retaining their status as “molecules of life”, are becoming “molecular wires”, materials for the construction of molecular structures at the junction between the biological and abiotic worlds. Herein, we present an overview of the approaches for incorporating metal centers into nucleic acids based on metal–boron cluster complexes (metallacarboranes) as the metal carriers. The methods are modular and versatile, allowing practical access to innovative metal-containing DNA for various applications, such as nucleic acid therapeutics, electrochemical biosensors, infrared-sensitive probes, and building blocks for nanoconstruction.

scholarly journals Reverse C-glycosidase reaction provides C-nucleotide building blocks of xenobiotic nucleic acids

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Martin Pfeiffer ◽  
Bernd Nidetzky
Keyword(s):  
Synthetic Biology ◽  
Nucleic Acids ◽  
Enzymatic Reaction ◽  
Building Blocks ◽  
Cascade Reactions ◽  
Ring Closure ◽  
One Pot ◽  
Open Chain ◽  
Nucleotide Synthesis ◽  
Nucleotide Triphosphates

AbstractC-Analogues of the canonical N-nucleosides have considerable importance in medicinal chemistry and are promising building blocks of xenobiotic nucleic acids (XNA) in synthetic biology. Although well established for synthesis of N-nucleosides, biocatalytic methods are lacking in C-nucleoside synthetic chemistry. Here, we identify pseudouridine monophosphate C-glycosidase for selective 5-β-C-glycosylation of uracil and derivatives thereof from pentose 5-phosphate (d-ribose, 2-deoxy-d-ribose, d-arabinose, d-xylose) substrates. Substrate requirements of the enzymatic reaction are consistent with a Mannich-like addition between the pyrimidine nucleobase and the iminium intermediate of enzyme (Lys166) and open-chain pentose 5-phosphate. β-Elimination of the lysine and stereoselective ring closure give the product. We demonstrate phosphorylation-glycosylation cascade reactions for efficient, one-pot synthesis of C-nucleoside phosphates (yield: 33 – 94%) from unprotected sugar and nucleobase. We show incorporation of the enzymatically synthesized C-nucleotide triphosphates into nucleic acids by RNA polymerase. Collectively, these findings implement biocatalytic methodology for C-nucleotide synthesis which can facilitate XNA engineering for synthetic biology applications.

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