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Phosphoramidite information


Phosphoramidite: general structure

A phosphoramidite (RO)2PNR2 is a monoamide of a phosphite diester. The key feature of phosphoramidites is their markedly high reactivity towards nucleophiles catalyzed by weak acids e.c., triethylammonium chloride or 1H-tetrazole. In these reactions, the incoming nucleophile replaces the NR2 moiety.

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Phosphoramidite

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A phosphoramidite (RO)2PNR2 is a monoamide of a phosphite diester. The key feature of phosphoramidites is their markedly high reactivity towards nucleophiles...

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Oligonucleotide synthesis

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process is implemented as solid-phase synthesis using phosphoramidite method and phosphoramidite building blocks derived from protected 2'-deoxynucleosides...

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Phosphoramidite ligand

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A phosphoramidite ligand is any phosphorus-based ligand with the general formula P(OR1)(OR2)(NRR'). Chiral versions of these ligands, particularly those...

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Nucleoside phosphoramidite

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Nucleoside phosphoramidites are derivatives of natural or synthetic nucleosides. They are used to synthesize oligonucleotides, relatively short fragments...

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Fluorescein

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oligonucleotide synthesis, several phosphoramidite reagents containing protected fluorescein, e.g. 6-FAM phosphoramidite 2, are used for the preparation...

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Nucleotide

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production of nucleotides. A purified nucleoside is protected to create a phosphoramidite, which can then be used to obtain analogues not found in nature and/or...

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Molar mass

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meaning when used in the context of DNA synthesis: whereas an individual phosphoramidite nucleobase to be added to a DNA polymer has protecting groups and has...

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Hybridization probe

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hybridized. Depending on the method, the probe may be synthesized using the phosphoramidite method, or it can be generated and labeled by PCR amplification or...

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Asymmetric hydrogenation

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bonded ligands, with P-heteroatom ligands like the phosphites and phosphoramidites generally achieving more impressive results. Structural classes of...

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Diethyl tartrate

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"Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone". Angew. Chem. Int. Ed. 49...

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Biotinylation

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course of oligonucleotide synthesis by the phosphoramidite method using commercial biotin phosphoramidite. Upon the standard deprotection, the conjugates...

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Tetrazole

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11, 1989). "Studies on the role of tetrazole in the activation of phosphoramidites". Nucleic Acids Res. 17 (3): 853–864. doi:10.1093/nar/17.3.853. PMC 331708...

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Threose nucleic acid

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solid-phase synthesis using phosphoramidite chemistry. Methods for chemically synthesized TNA monomers (phosphoramidites and nucleoside triphosphates)...

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Oligonucleotide

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Oligonucleotides are chemically synthesized using building blocks, protected phosphoramidites of natural or chemically modified nucleosides or, to a lesser extent...

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DNA synthesis

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even chromosomes. Today, all synthetic DNA is custom-built using the phosphoramidite method by Marvin H. Caruthers. Oligos are synthesized from building...

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Fluorescein amidite

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molecular beacons. The commercially available 6-FAM version is shown in the figure. US 5583236, Brush, C. K., "Fluorescein Labelled Phosphoramidites" ...

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Phosphoramidate

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phosphorodiamidate is morpholino which is used in molecular biology. Phosphoramidite IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book")...

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Hot start PCR

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protecting group that is photochemically removable, such as caged thymidine phosphoramidites, is incorporated into a oligonucleotide primer.  This allows the function...

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Biopolymer

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sequence Food microbiology § Microbial biopolymers Melanin Non food crops Phosphoramidite Polymer chemistry Sequence-controlled polymers Sequencing Small molecules...

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Ben Feringa

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Feringa's work has crossed many disciplines and includes the use of phosphoramidites as ligands in asymmetric catalysis, an excellent stereocontrol was...

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Leroy Hood

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Boulder, and was based on Caruthers' work elucidating the chemistry of phosphoramidite oligonucleotide synthesis. Caltech staff scientist Suzanna J. Horvath...

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Molecular beacon

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set of nucleoside phosphoramidites, the synthesis also requires a solid support derivatized with a quencher and a phosphoramidite building block designed...

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NS5B inhibitor

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nucleoside inhibitors. Sofosbuvir is a pyrimidine nucleoside analog and a phosphoramidite prodrug. The isomeric form of the amino acid matters since the D-alanine...

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Protecting group

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Radhakrishman P. Iyer: "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach", in: Tetrahedron, 1992, 48, pp. 2223–2311; doi:10...

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Acetonitrile

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dominant solvent used in oligonucleotide synthesis from nucleoside phosphoramidites. Industrially, it is used as a solvent for the manufacture of pharmaceuticals...

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Artificial gene synthesis

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are chemically synthesized using building blocks called nucleoside phosphoramidites. These can be normal or modified nucleosides which have protecting...

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Nucleic acid analogue

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synthesized enzymatically and can only be obtained synthetically using the phosphoramidite strategy or, for PNA, other methods of peptide synthesis.[citation...

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Fine chemical

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507.2. Oligonucleotides are chemically synthesized from protected phosphoramidites of natural or chemically modified nucleosides. The oligonucleotide...

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