- A convenient route to synthesize N2-(isobutyryl)-9-(carboxymethyl)guanine for aeg-PNA backbone
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Synthesis of exclusive N2-(isobutyryl)-9-(carboxymethyl)guanine, an important moiety for peptide nucleic acid synthesis has been reported through a high-yielding reaction scheme starting from 6-chloro-2-amino purine. Crystal structures of two intermediates confirmed the formation of N9-regioisomer. This new synthetic route can potentially replace the conventional tedious method with moderate overall yield.
- Datta, Dhrubajyoti
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- Peptide Nucleic Acid with Double Face: Homothymine-Homocytosine Bimodal Cα-PNA (bm-Cα-PNA) Forms a Double Duplex of the bm-PNA2:DNA Triplex
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Cα-bimodal peptide nucleic acids (bm-Cα-PNA) are PNAs with two faces and are designed homologues of PNAs in which each aminoethylglycine (aeg) repeating unit in the standard PNA backbone hosts a second nucleobase at Cα through a spacer chain with a triazole linker. Such bm-Cα-PNA with mixed sequences can form double duplexes by simultaneous binding to two complementary DNAs, one to the base sequence on t-amide side and the other to the bases on the Cα side chain. The synthesis of bm-Cα-PNA with homothymine (T7) on the t-amide face and homocytosine (C5) on the Cα side chain through the triazole linker was achieved by solid phase synthesis with the global click reaction. In the presence of complementary DNAs dA8 and dG6 at neutral pH, bm-Cα-PNA 1 forms a higher order pentameric double duplex of a triplex composed of two bm-Cα-PNA-C5:dG5 duplexes built on a core (bm-Cα-PNA-T7)2:dA8 triplex. Circular dichroism studies showed that assembly can be achieved by either triplex first and duplex later or vice versa. Isothermal titration calorimetry data indicated that the assembly is driven by favorable enthalpy. These results validate concurrent multiple complex formation by bimodal PNAs with additional nucleobases at Cα or Cγon the aeg-PNA backbone and open up ways to design programmed supramolecular assemblies.
- Gupta, Manoj Kumar,Madhanagopal, Bharath Raj,Ganesh, Krishna N.
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supporting information
p. 414 - 428
(2020/12/22)
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- PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS
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Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moie
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- Synthesis of photolabile o-nitroveratryloxycarbonyl (NVOC) protected peptide nucleic acid monomers
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The chemical synthesis of peptide nucleic acid (PNA) monomers was accomplished using various combinations of the o-nitroveratryloxycarbonyl (NVOC) group (N-aminoethylglycine backbone) and base labile acyl-type nucleobase protecting groups (anisoyl for ade
- Liu, Zheng-Chun,Shin, Dong-Sik,Lee, Kyu-Teak,Jun, Bong-Hyun,Kim, Yong-Kweon,Lee, Yoon-Sik
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p. 7967 - 7973
(2007/10/03)
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- PNA-directed triple-helix formation by N7-xanthine
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We report the first example of alkylation of underivatized xanthine with chloroacetic acid to yield a separable mixture of N7- and N 9-(methylenecarboxyl)xanthine and its conversion to a peptide nucleic acid monomer compatible with Fmoc-based oligomerization chemistry. Additionally, we have simultaneously prepared the N7- and N 9-PNA monomers of guanine by alkylation of 2-N-isobutyrylguanine which were subsequently separated. Molecular modeling of the nucleobase base triplets indicates that N7-xanthine and N7-guanine form isomorphous triplets with adenine and guanine, respectively. We also show that polyamides containing N7-xanthine are compatible with triple-helix formation. Georg Thieme Verlag Stuttgart.
- Hudson, Robert H. E.,Goncharenko, Mykhaylo,Wallman, Andrew P.,Wojciechowski, Filip
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p. 1442 - 1446
(2007/10/03)
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- Substituted N-ethylglycine derivatives for preparing PNA and PNA/DNA hybrids
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There are described N-ethylglycine derivatives of the formula I in which PG is a urethane-type or trityl-type amino protective group which is labile to weak acids, X is NH, O or S, Y is CH2, NH or O, and B' are bases customary in nucleotide chemistry, the exocyclic amino or hydroxyl groups of which being protected by suitable, known protective groups, or are base substitute compounds, and their salts with tert-organic bases, as well as a process for their preparation. The N-ethylglycine derivatives of the formula I are used in the preparation of PNA and PNA/DNA hybrids.
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- The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy
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The preparation of novel monomethoxytrityl (Mmt) protected monomers for the synthesis of polyamide nucleic acids (PNAs) is described. The use of base-labile acyl-type nucleobase protecting groups and of a succinyl-linked solid-support offers a synthetic strategy to standard oligonucleotide synthesis conditions. This strategy has been successfully applied for the synthesis of PNAs of mixed base sequence.
- Will, David W.,Breipohl, Gerhard,Langner, Dietrich,Knolle, Jochen,Uhlmann, Eugen
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p. 12069 - 12082
(2007/10/02)
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