Preparation of Modified RNA Sequences for Biological Research

Pitsch, Stefan; Ackermann, Damian; Denarie, Cyrille; Meylan, Frederic; Meyyappan, Muthulaniappan; Müller, Emil; Peer, Andreas; Porcher, Sébastien; Reymond, Luc; Stutz, Alfred; Wenter, Phillipp; Wu, Xiaolin

doi:10.2533/000942905777675633

Cited by 6 publications

(7 citation statements)

References 13 publications

(14 reference statements)

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“…C 24 H 44 N 2 O 9 Si 2 Na requires 583.775). -(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)uridine (5). Compound 5 (10 mg, 0.018 mmol) and 1H-tetrazole (25 mg, 0.36 mmol) were dissolved in CDCl 3 -DMSO-d 6 (5:1 v/v, 0.6 ml) in an NMR tube.…”

Section: Resultsmentioning

confidence: 99%

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Chemical Properties of 4,5‐Di(ethoxycarbonyl)‐1,3‐dioxolan‐2‐yl (DECDO) as a Hydroxyl Protecting Group of the 2′‐Hydroxyl Function in Ribonucleosides.

2007

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Nucleic acids U 0700Chemical Properties of 4,5-Di(ethoxycarbonyl)-1,3-dioxolan-2-yl (DECDO) as a Hydroxyl Protecting Group of the 2'-Hydroxyl Function in Ribonucleosides. -The DECDO group in uridine (III) is compatible with the DMTr strategy for the currently used oligonucleotide synthesis. Post-synthetic treatment with ammonia results in the conversion of the DECDO into the dicarbamoyldioxolanyl (DCBDO) group, cf. (X), which is more stable under acidic conditions than the DECDO group. These groups can be considered as typical protecting groups for the hydroxyl function as well as new protecting groups of the orthoester-type in nucleic acid and carbohydrate chemistry. The stability of the DCBDO group increases but this group remains removable under moderate conditions in alcohol/water solutions. The methoxymethyl and dioxolanyl groups in (III) are weak as secondary alcohol protecting groups, but can be used if mild acidic conditions are necessary. -(KARWOWSKI*, B.; SEIO, K.; SEKINE, M.; J. Heterocycl. Chem. 44 (2007) 2, 329-336; Dep. Life Sci., Tokyo Inst. Technol., Midori, Yokohama 226, Japan; Eng.) -H. Hoennerscheid 32-205

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Section: Resultsmentioning

confidence: 99%

“…Although a number of hydroxyl protecting groups have been explored, [1][2][3][4][5][6][7][8] only a few have survived in the field of nucleoside and nucleotide chemistry. This is due to the strict conditions which are required for their chemical transformation.…”

Section: Introductionmentioning

confidence: 99%

Chemical Properties of 4,5‐Di(ethoxycarbonyl)‐1,3‐dioxolan‐2‐yl (DECDO) as a Hydroxyl Protecting Group of the 2′‐Hydroxyl Function in Ribonucleosides.

2007

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“…d) Ribopyranose phosphate formation. [23] e) Intramolecular boronic ester formation as cyclisation method.…”

Section: Introductionmentioning

confidence: 99%

“…Cyclic phosphates of ribopyranose, such as the cyclo-2,4phosphate shown in Figure 1d), were described. [23] Furthermore, ribopyranose forms complexes with metals such as Ca 2 + (for experimental details see Figure 6), Y 3 + , La 3 + (Figure 1c). [24,25,26] From the possible applications shown in Figure 1, the boronic ester formation with a chromophore (b) and the metal binding properties (c) are covered in this present work.…”

Section: Introductionmentioning

confidence: 99%

Reversible Boronic Ester Formation of Ribopyranosylated Glycopeptides

Kirschner

Geyer

2016

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Six natural amino acids bearing hydroxy or thiol groups are transformed into N‐Fmoc and O‐acetyl protected ribopyranosylated amino acids (Raa) for further use in solid‐phase peptide synthesis (SPPS). Although the different O‐ and S‐glycosidic bonds influence the 1C4/4C1 equilibrium of the ribopyranosyl side chain significantly, the oligopeptides containing Raa are capable of spontaneous boronic ester formation. Ligation of model peptides with pyrene boronic acid and competition experiments between different peptides are monitored by NMR spectroscopy. In addition to boronic ester formation, we further propose ribopyranosylated peptides with adjustable orientation of the trihydroxy ax‐eq‐ax disposition for other applications.

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“…Das Schützen der reaktiven funktionellen Gruppen ist ein häufiger Schritt bei der maschinellen Synthese von komplexen Molekülen wie Peptiden, Oligosacchariden, DNA und RNA, [2] und die Vielzahl an Anwendungen in der Biologie und Medizin ist unmittelbar der Verwendung von Schutzgruppenstrategien zu verdanken. Auch zur Synthese kleinerer Moleküle werden Schutzgruppentechniken intensiv genutzt, z.…”

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