Phosphite Oxidation and the Preparation of Five-Membered Cyclic Phosphorylating Reagents Via the Phosphites

Ugi, Ivar; Jacob, P.; Landgraf, B.; Ruppf, C.; Lemmen, Peter; Verfürth, Uwe

doi:10.1080/07328318808056294

Cited by 20 publications

(13 citation statements)

References 9 publications

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“…31 Figure 3C shows the resulting improvement in feature uniformity. This is reflected quantitatively in a lower standard deviation without any loss in signal intensity (Figure 3D), although some variation is still evident in the array images.…”

Section: Resultsmentioning

confidence: 99%

Photolithographic Synthesis of High-Density DNA and RNA Arrays on Flexible, Transparent, and Easily Subdivided Plastic Substrates

Holden

Carter

et al. 2015

Anal. Chem.

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The photolithographic fabrication of high-density DNA and RNA arrays on flexible and transparent plastic substrates is reported. The substrates are thin sheets of poly(ethylene terephthalate) (PET) coated with crosslinked polymer multilayers that present hydroxyl groups suitable for conventional phosphoramidite-based nucleic acid synthesis. We demonstrate that by modifying MAS procedures to accommodate the physical and chemical properties of these materials, it is possible to synthesize plastic-backed oligonucleotide arrays with feature sizes as small as 14 × 14 μm and feature densities in excess of 125 000/cm2, similar to specifications attainable using rigid substrates such as glass or glassy carbon. These plastic-backed arrays are tolerant to a wide range of hybridization temperatures, and improved synthetic procedures are described that enable the fabrication of arrays with sequences up to 50 nucleotides in length. These arrays hybridize with S/N ratios comparable to those fabricated on otherwise identical arrays prepared on glass or glassy carbon. This platform supports the enzymatic synthesis of RNA arrays and proof-of-concept experiments are presented showing that the arrays can be readily sub-divided into smaller arrays (or ‘millichips’) using common laboratory-scale laser cutting tools. These results expand the utility of oligonucleotide arrays fabricated on plastic substrates and open the door to new potential applications for these important bioanalytical tools.

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Section: Resultsmentioning

confidence: 99%

Photolithographic Synthesis of High-Density DNA and RNA Arrays on Flexible, Transparent, and Easily Subdivided Plastic Substrates

Holden

Carter

et al. 2015

Anal. Chem.

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“…We substituted iodine with (1S)-(+)-(10-camphorsulfonyl)oxaziridine (CSO), 14 as the oxidizing reagent because in our experiments CSO led to purer target products. The coupling step requires two reagents, phosphoramidite and 5-ethylthio-1Htetrazole as activators.…”

mentioning

confidence: 99%

Solvent resistant microfluidic DNA synthesizer

et al. 2007

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“…This protocol combined phosphoramidite and H -phosphonate chemistries, and allowed the introduction of phosphoramidate and phosphonamidate linkages at specific sites of the oligonucleotide 25 (Scheme 5). We found that the H -phosphonate and O -methyl-( H )-phosphinate internucleotide linkages in oligonucleotide 26 were neither cleaved nor oxidized by oxaziridine CSO [24,25,26] which represented a mild phosphoramidite oxidation agent. This reagent allowed selective oxidation of P III linkage in the presence of H -phosphonate or H -phosphinate bonds.…”

Section: Resultsmentioning

confidence: 99%

Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

et al. 2019

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We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands.

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Phosphite Oxidation and the Preparation of Five-Membered Cyclic Phosphorylating Reagents Via the Phosphites

Cited by 20 publications

References 9 publications

Photolithographic Synthesis of High-Density DNA and RNA Arrays on Flexible, Transparent, and Easily Subdivided Plastic Substrates

Photolithographic Synthesis of High-Density DNA and RNA Arrays on Flexible, Transparent, and Easily Subdivided Plastic Substrates

Solvent resistant microfluidic DNA synthesizer

Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

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