Novel oligonucleotide analogues containing a morpholinoamidine unit

Pérez-Rentero, Sónia; Alguacil, Javier; Robles, Jordi

doi:10.1016/j.tet.2008.11.069

Cited by 17 publications

(9 citation statements)

References 62 publications

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“…Notably, a homopyrimidine DNA oligonucleotide incorporating a single 3'-morpholinoamidine subunit designed as a TFO, hybridised with a 23-mer duplex DNA containing a sequence targetable by the TFO, at every pH studied. [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: 99%

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: 99%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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“…[5] Morpholino-modified nucleotides contain regular DNA bases with the modification of the deoxyribose rings by morpholine rings, linked through phosphorodiamidate linkages ( Figure 1). Modified oligonucleotides (DNA or siRNA) [6,7] containing single morpholino units (T-or Umorpholino) show better efficacy for gene silencing and better resistance towards nuclease activity. [8] Applications of MO oligomers are not limited only to antisense activity; these oligomers have also found growing applications in groups remain at the end.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Nandi¹,

Pattanayak²,

Paul³

et al. 2013

Eur J Org Chem

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Morpholino‐modified nucleoside analogues have widespread applications in developmental biology. To achieve nucleobase‐functionalized forms of morpholino nucleosides, syntheses of 5‐substituted cytidine, 8‐substituted adenosine, and 8‐substituted guanosine morpholino nucleoside monomers are described for the first time. The syntheses are based on the use of 5‐iodocytidine, 8‐bromoadenosine, and 8‐bromoguanosine morpholino nucleosides as the key starting materials. These iodo or bromo derivatives have also been synthesized for the first time. Palladium‐mediated cross‐coupling reactions (Sonogashira, Suzuki, and Heck) were then employed with the halo derivatives to accomplish the substitutions. Different reaction conditions for C, A, and G were standardized to achieve the conversions. The strategy was devised in such a way that the useful N‐trityl protecting groups remain at the end. The catalyst combinations used for Sonogashira, Suzuki, and Heck reactions were Pd(PPh3)2Cl2·CuI, Pd(dppf)Cl2·CH2Cl2, and Pd(OAc)2, respectively. Heck coupling between 5‐iodocytidine monomer and methyl acrylate worked well, whereas with acrylonitrile the exocyclic amine of cytidine was found to form the aza‐Michael adduct. In this context, treatment of iodocytidine with methyl acrylate under two different sets of conditions was found to produce either the Michael addition product or the Heck coupling product. Four of the functionalized morpholino monomers have been further confirmed by single‐crystal X‐ray structural analysis. All of these functionalized monomers were obtained in good to excellent overall yields.

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“…Among the various modifications of DNA strands, base or sugar changes (Eppacher et al, 2000;Lee and Kool, 2009;Perez-Rentero et al, 2009;Roig and Asseline, 2009), those of internucleosidic linkers are very promising, since they render the backbone virtually insensitive to acid/alkaline or enzymatic hydrolysis. In the context of the antisense therapy, single strands of modified DNA must form stable complexes with natural DNA or RNA.…”

Section: Introductionmentioning

confidence: 99%

Biological investigation using a shear horizontal surface acoustic wave sensor: Small “Click generated” DNA hybridization detection

Zerrouki¹,

Fourati²,

Lucas³

et al. 2010

Biosensors and Bioelectronics

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Novel oligonucleotide analogues containing a morpholinoamidine unit

Cited by 17 publications

References 62 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Biological investigation using a shear horizontal surface acoustic wave sensor: Small “Click generated” DNA hybridization detection

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