New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether

Abramova, Tatyana V.; Kassakin, Marat F.; Lomzov, Alexander A.; Pyshnyi, D. V.; Silnikov, Vladimir N.

doi:10.1016/j.bioorg.2006.12.003

Cited by 12 publications

(13 citation statements)

References 32 publications

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“…[33] Silnikov et al have synthesised a morpholino analogue containing an oxalyl diamide linker (20); at present an oligonucleotide with sufficient length has not been synthesised to produce a detectable T m , but further studies are ongoing (Scheme 4). [34] …”

Section: Sugar Modificationsmentioning

confidence: 97%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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Although known for more than a century, bromine trifluoride is not a common reagent in day to day research work in organic chemistry. Its tendency to react exothermically with solvents containing Lewis base elements such as water, acetone or ethers distanced it from the mind of many. Still, under the proper conditions, it can perform quite a few selective reactions which are difficult to achieve by other reagents. We discuss in this review reactions which have been published in the last 30 years. They consist of fluorinating heteroatoms, substituting carbon‐halogen bonds with carbon‐fluorine bonds, syntheses of anesthetics, construction of the trifluoromethyl (CF3) and the difluoromethylene (CF2) groups, aromatic brominations and more.

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Section: Sugar Modificationsmentioning

confidence: 97%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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“…2) [8]. So, the oxalyl residue can be used as a labile linker between the solid support and the growing oligomer chain (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…We synthesized Boc-protected aminomethylmorpholino nucleosides 2a,d,e as shown in Scheme 1 starting from aminomethylmorpholino nucleosides 3a,d,e . The synthesis of adenine and uracil containing compounds 3a,d was published earlier [8]. Thymine containing morpholino nucleoside 3e was obtained similarly to 3d starting from the 5-methyluridine.…”

Section: Resultsmentioning

confidence: 99%

“…An attractive feature of these new morpholino oligonucleotide analogues is the absence of additional chiral centers. Unlike commercially available PMO and PPMO, which are mixtures of diastereomers, oligomers constructed with the use of phosphoromonoamidate [7], oxalyl diamide [8], amidine [9] and methylene caxboxamide [10] groups represent the individual compounds. It means that their physicochemical properties, such as thermostability of complementary complexes, do not depend on the diastereomeric composition of the mixtures, which can vary in different preparations.…”

Section: Introductionmentioning

confidence: 99%

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Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

Abramova¹,

Belov²,

Tarasenko³

et al. 2014

Beilstein J. Org. Chem.

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“…However, oligouridylate analogues, in which monomer units are joined with a tight oxalate linker (Id), could not form stable complementary complexes with native nucleic acids [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of nucleic acid methylene carboxamide mimics derived from morpholine nucleosides

et al. 2012

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Uracyl and adenine containing oligocarboxamide mimetics of nucleic acids based on morpholine nucleosides (MorGly) are synthesized using peptide chemistry methods. Conditions for an analysis of homogeneity of protonated at physiological pH oligomers using a capillary electrophoresis are proposed. Studies of thermostability of complementary complexes formed by MorGly oligomers revealed that melting temperature dramatically depends on heterocyclic base composition (uracyl or adenine). Cooperative interactions realized at junctions in tandem complexes give more contribution to the thermostability in the case of complexes formed by modified oligomers than native oligodeoxyriboadenilates. Adenine containing MorGly oligomers form more stable complexes with poly(U) than native oligodeoxyriboadenilate of the same length. Complexes formed by modified oligomers with polyribonucleotides are more stable in compare with polydeoxyribonucleotide.

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New oligonucleotide analogues based on morpholine subunits joined by oxalyl diamide tether

Cited by 12 publications

References 32 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Solid-phase-supported synthesis of morpholinoglycine oligonucleotide mimics

Synthesis and properties of nucleic acid methylene carboxamide mimics derived from morpholine nucleosides

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