83467-48-5Relevant articles and documents
COMPOSITIONS AND METHODS FOR CHEMICAL CLEAVAGE AND DEPROTECTION OF SURFACE-BOUND OLIGONUCLEOTIDES
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Paragraph 0199; 0201; 0203, (2019/12/01)
Embodiments of the present disclosure relate to methods of preparation of templates for polynucleotide sequencing. In particular, the disclosure relates to linearization of clustered polynucleotides in preparation for sequencing by cleavage of one or more first strands of double-stranded polynucleotides immobilized on a solid support by a transition metal complex, for example, a palladium complex or a nickel complex. Further disclosure relate to linearization of clustered polynucleotides by cleaving one or more second strands of double double-stranded polynucleotides immobilized on a solid support comprising azobenzene linker by Na2S2O4. Nucleotides and oligonucleotides comprising a 3′ phosphate moiety blocking group, and methods of removing the same using a fluoride reagent are also disclosed.
NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS
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Paragraph 0345-0346, (2019/11/04)
The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.
THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS
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Page/Page column 91; 92, (2018/11/10)
The present invention relates to chemical linkers and protecting groups, compounds and compositions containing the chemical linkers or protecting groups, and intermediates and processes that can be used to prepare them. The chemical linkers and protecting groups are based on pyrrolidine and piperidine activating groups, which undergo intramolecular cyclisation upon heating with release of carbon dioxide, thereby releasing the organic compound from a substrate. In particular, those chemical linkers and protecting groups are useful in the solid phase synthesis of oligonucleotides according to the following representative schemes.
COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS
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Paragraph 001759; 001762; 001763, (2019/01/10)
The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.
An organocatalyzed Stetter reaction as a bio-inspired tool for the synthesis of nucleic acid-based bioconjugates
Hamoud, Aladin,Barthélémy, Philippe,Desvergnes, Valérie
, p. 1760 - 1769 (2018/03/21)
An N-Heterocyclic Carbene (NHC) catalyzed biomimetic Stetter reaction was applied for the first time as a bioconjugation reaction to sensitive nucleoside-type biomolecules to provide original pyrrole linked nucleolipids. A versatile approach allowed the functionalization of thymidine at the three reactive positions (O-5′, O-3′ and N-3) providing a structural diversity oriented synthesis. This strategy was applied to the synthesis of an original glyconucleolipid amphiphile in the hope that the pyrrole aromatic moiety would induce additional self-assembling properties.
Copper(II)nitrate catalyzed regioselective protection of primary alcohols with 4,4′-dimethoxytrityl and 2,7-dimethyl-9-phenyl xanthen-9-yl groups in nucleosides and carbohydrates
Penjarla, Srishylam,Prasad, S. Rajendra,Reddy, Dhande Sudhakar,Banerjee, Shyamapada,Penta, Santhosh,Sanghvi, Yogesh S.
, p. 232 - 247 (2018/05/14)
Regioselective protection of primary hydroxyl group in nucleoside and carbohydrate analogs was accomplished using dimethoxytrityl alcohol (DMTr-OH) or dimethylpixyl alcohol (DMPx-OH) in presence of copper(II)nitrate as a Lewis acid catalyst. Excellent selectivity was observed for the protection of primary hydroxyl group over secondary while glycosidic bond remain unaffected. Utility of this methodology was further exemplified via DMTr- and DMPx-protection of alipahtic acyclic and cyclic diols.
Synthesis and structural study of ribo-dioxaphosphorinane-constrained nucleic acid dinucleotides (ribo-α,β-D-CNA)
Maturano, Marie,Catana, Dan-Andrei,Lavedan, Pierre,Tarrat, Nathalie,Saffon, Nathalie,Payrastre, Corinne,Escudier, Jean-Marc
scheme or table, p. 721 - 730 (2012/04/18)
With increasing interest in the control of the conformations of nucleic acids to define active riboswitch or siRNA, we present herein our efforts towards the stereocontrolled synthesis and conformational analysis of ribodinucleotides in which α and β torsional angles are constrained within a dioxaphosphorinane structure (ribo-α,β-D-CNA). The crystal structure analysis of one α,β-D-CNA TU dimer demonstrates the absolute stereochemistry of the newly created asymmetric centres. NMR and CD analyses allowed complete assignment and the determination of the torsional angles in the α,β-D-CNA UU diastereoisomers. Diastereoisomers of α,β-D-CNA ribodinucleotide building blocks of nucleicacids in which the α and β torsional angles are stereocontrolled by a dioxaphosphorinane ring structure (D-CNA family) have been synthesised. The structural analyses showed that these dinucleotides exhibit a South/North junction associated with either canonical or non-canonical states of the sugar phosphate backbone. Copyright
Non-standard nucleobases implementing the isocytidine and isoguanosine hydrogen bonding patterns
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Page/Page column 17, (2010/07/02)
This invention provides compositions of matter that, when incorporated into an oligonucleotide, present to a complementary strand in a Watson-Crick pairing geometry a pattern of hydrogen bonds that is different from the pattern presented by adenine, guani
Oligonucleotides having A-DNA form and B-DNA form conformational geometry
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, (2008/06/13)
Modified oligonucleotides containing both A-form conformation geometry and B-from conformation geometry nucleotides are disclosed. The B-form geometry allows the oligonucleotide to serve as substrates for RNase H when bound to a target nucleic acid strand. The A-form geometry imparts properties to the oligonucleotide that modulate binding affinity and nuclease resistance. By utilizing C2′ endo sugars or O4′ endo sugars, the B-form characteristics are imparted to a portion of the oligonucleotide. The A-form characteristics are imparted via use of either 2′-O-modified nucleotides that have 3′ endo geometries or use of end caps having particular nuclease stability or by use of both of these in conjunction with each other.
New and efficient synthesis of 5′-amino-5′-(S)-methyl-2′,5′-dideoxynucleosides
Jung, Pierre M. J.,Beaudegnies, Renaud,De Mesmaeker, Alain,Wendeborn, Sebastian
, p. 293 - 297 (2007/10/03)
A short, efficient synthesis of 5′-amino-5′-(S)-methyl-2′,5′-dideoxynucleosides 1 has been developed through the diastereoselective addition of methylmagnesium bromide or methyllithium to an intermediate tert-butylsulfinimide.
