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            ‐Phenylene Carbonate

Hanslick, R. S.; Bruce, William F.; Mascitti, A.

doi:10.1002/0471264180.os033.29

Cited by 2 publications

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“…1,4-Dimethoxycatechol 11 was synthesized following published procedures 24 from commercially available catechol. Cyclic 1,4-dimethoxycatechol 12 was prepared from 1,4-dimethoxycatechol following published procedures, 37 except N,N′-carbonyldiimidazole was substituted for phosgene. Product 12 was confirmed on a TLC plate eluted in dichloromethane (DCM).…”

Section: Methodsmentioning

confidence: 99%

A Novel Catechol-Based Universal Support for Oligonucleotide Synthesis

et al. 2007

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A novel universal support for deoxyribo- and ribonucleic acid synthesis has been developed. The support, constructed from 1,4-dimethoxycatechol, represents an improvement over existing universal supports because of its ability to cleave and deprotect under mild conditions in standard reagents. Because no nonvolatile additives are required for cleavage and deprotection, the synthesized oligonucleotides do not require purification prior to use in biochemical assays. Using reverse phase HPLC and electrospray mass spectroscopy, it was determined that oligonucleotides synthesized on the universal support (UL1) 3'-dephosphorylate quickly (9 h in 28-30% ammonium hydroxide (NH4OH) at 55 degrees C, 2 h in 28-30% NH4OH at 80 degrees C, or <1 h in ammonium hydroxide/methylamine (1:1) (AMA) at 80 degrees C). Oligonucleotides used as primers for the polymerase chain reaction (PCR) assay were found to perform identically to control primers, demonstrating full biological compatibility. In addition, a method was developed for sintering the universal support directly into a filter plug which can be pressure fit into the synthesis column of a commercial synthesizer. The universal support plugs allow the synthesis of high-quality oligonucleotides at least 120 nucleotides in length, with purity comparable to non-universal commercial supports and approximately 50% lower reagent consumption. The universal support plugs are routinely used to synthesize deoxyribo-, ribo-, 3'-modified, 5'-modified, and thioated oligonucleotides. The flexibility of the universal support and the efficiency of 3'-dephosphorylation are expected to increase the use of universal supports in oligonucleotide synthesis.

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Section: Methodsmentioning

confidence: 99%

A Novel Catechol-Based Universal Support for Oligonucleotide Synthesis

et al. 2007

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“…The protocol was adapted from Hanslick et al 33 . 5.0 g (0.04 mol) of catechol was added to 11 ml of a 26% aqueous solution of sodium hydroxide in a round bottom flask, which was then placed on an ice bath.…”

Section: Synthesis Of O-phenylene Carbonate (3)mentioning

confidence: 99%

Catechol-Vanadate Analogues as β-Lactamase Inhibitors

Yee¹

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Studying the Mechanism of Vanadate Catechol inhibition, and the Development of New β-lactamase Inhibitors……………………………………………………...…..21 II. Materials and Methods Materials, Instrumentation, and Analysis ……………………………………….…..23 Synthesis and Characterization of dicyclohexylammonium o-phenylene phosphate (1a)…………………………………………………………………………………..24 Kinetic Experiments with 1a………………………………………………………...27 Synthesis and Characterization of o-(4-nitrophenylene) carbonate (2)……….…..28 Kinetic Experiments with 2……………………………………………………….....29 Synthesis and Characterization of o-phenylene carbonate (3)…………………...….31 Kinetic Experiments with 3………………………………………………………....32 Determination of Rate Constants……………………………………………………33 III. Results Synthesis and Characterization of dicyclohexylammonium o-phenylene phosphate (1a)…………………………………………………………………………………...35 Kinetic Experiments with 1a………………………………………………………...38 Synthesis and Characterization of o-(4-nitrophenylene) carbonate (2)……………...44 Kinetic Experiments with 2………………………………………………………….46 Synthesis and Characterization of o-phenylene carbonate (3)………………………59 Kinetic Experiments with 3………………………………………………………….61 IV. Discussion……………………………………………………………………….71 V. Conclusions and Future Work………………………………………………….75 VI. References………………………………………………………………………76 V1I. Appendix A: Synthesis of o-phenylene phosphate (1)………………..…………………...78 B: Synthesis of o-(4-nitrophenylene) carbonate (2)………………………………..85 C: Synthesis of o-phenylene carbonate (3)………………………………………...86 D: Example of an Dynafit analysis…………………………………………………..87

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o ‐Phenylene Carbonate

Abstract: o ‐phenylene carbonate product: o ‐phenylene carbonate

Cited by 2 publications

References 0 publications

A Novel Catechol-Based Universal Support for Oligonucleotide Synthesis

A Novel Catechol-Based Universal Support for Oligonucleotide Synthesis

Catechol-Vanadate Analogues as β-Lactamase Inhibitors

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