Conformational analysis of 3′‐fluorinated A(2′‐5′)A(2′‐5′)A fragments

Boogaart, Jacquelien E. van den; Kalinichenko, Еlena N.; Podkopaeva, Tatjana L.; Mikhailopulo, Igor A.; Altona, C.

doi:10.1111/j.1432-1033.1994.tb18789.x

Cited by 17 publications

(1 citation statement)

References 37 publications

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“…1 H NMR studies of nucleotides are typically performed at concentrations of tens of millimoles per litre [39Ϫ 43], in some cases up to more than 100 mM [42]; others have used a 600-MHz instrument in which about 5 mM solution has been measured [43]. As a rule, nucleotides are pretreated with cation-exchange resins, lyophilized several times from highly enriched 2 H 2 O and the final solution is prepared in 99.9% 2 H 2 O.…”

Section: Nmr Analysismentioning

confidence: 99%

Identification of the reaction products of (2′‐5′)oligoadenylate synthetase in the marine sponge

Kuusksalu¹,

Subbi²,

Pehk³

et al. 1998

European Journal of Biochemistry

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Previously we reported on the presence of a high (2′-5′)oligoadenylate synthetase activity in the marine sponge Geodia cydonium [Kuusksalu, A., Pihlak, A., Müller, W. E. G. & Kelve, M. (1995) Eur. J. Biochem. 232, 351Ϫ357]. The presence of (2′-5′)oligoadenylates [(2′-5′)A] in crude sponge extract was shown by radioimmunoassay and by their HPLC comigration with authentic (2′-5′)A oligomers. In addition, the sponge (2′-5′)oligoadenylates displayed biological activity, as determined by inhibition studies of protein biosynthesis in rabbit reticulocyte lysate. In the present study individual (2′-5′)oligoadenylates synthesized by sponge enzyme were separated by HPLC. The exact composition of every oligonucleotide peak eluted was determined by matrix-assisted laser-desorption-ionization mass spectrometry (MALDI-MS) analysis. The 2′-5′ phosphodiester bond in oligoadenylates was verified by NMR analysis. Based on the high concentration of (2′-5′)A oligomers in G. cydonium and their similarity with those found in mammals we propose that the (2′-5′)A system is involved in a cytokine-mediated pathway and/ or in a protection system against viruses, present in the marine environment.Keywords : (2′-5′)oligoadenylate; Geodia cydonium ; matrix-assisted laser-desorption-ionization MS; NMR.Sponges (Porifera) are the simplest multicellular animals, which have existed since the Proteozoic period [1]. In the past few years several cDNA/gene sequences have been isolated and characterized from sponges, especially from the marine demosponge Geodia cydonium. Analyses revealed that sponges contain proteins of the extracellular matrix/basal lamina (e.g. integrin receptor [2], collagen [3] or galectin [4,5]), cell-surface receptors (tyrosine kinase receptor [6]), elements of the sensory system (crystallin [7], metabotropic glutamate receptor [8]) and homologs/modules of an immune system (immunoglobulin-like domains [9], scavenger receptor cysteine-rich domains and short consensus repeats [10], Rh-like protein [11]). These molecules were found to display high similarity to sequences from members of higher metazoan phyla [12].Recently a cDNA encoding a putative cytokine, the endothelial monocyte-activating polypeptide [13], was identified in G. cydonium [14]. The physiological role of this factor in sponges is not known. One pathway in mammalian organisms which is controlled by cytokine(s) is the (2′-5′)oligoadenylate [2′-5′(A)] system. It regulates the RNA degradation pathway and is inCorrespondence to M. Kelve,

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Section: Nmr Analysismentioning

confidence: 99%

Identification of the reaction products of (2′‐5′)oligoadenylate synthetase in the marine sponge

Kuusksalu¹,

Subbi²,

Pehk³

et al. 1998

European Journal of Biochemistry

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Synthesis and Application of gem‐Difluoromethylenated and Trifluoromethylated Building Blocks

Qing

Qiu²

2012

Efficient Preparations of Fluorine Compounds

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Synthesis of 3′‐Fluoro‐tRNA Analogues for Exploring Non‐ribosomal Peptide Synthesis in Bacteria

et al. 2015

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Aminoacyl-tRNAs (aa-tRNAs) participate in a vast repertoire of metabolic pathways, including the synthesis of the peptidoglycan network in the cell walls of bacterial pathogens. Synthesis of aminoacyl-tRNA analogues is critical for further understanding the mechanisms of these reactions. Here we report the semi-synthesis of 3'-fluoro analogues of Ala-tRNA(Ala) . The presence of fluorine in the 3'-position blocks Ala at the 2'-position by preventing spontaneous migration of the residue between positions 2' and 3'. NMR analyses showed that substitution of the 3'-hydroxy group by fluorine in the ribo configuration favours the S-type conformation of the furanose ring of terminal adenosine A76. In contrast, the N-type conformation is favoured by the presence of fluorine in the xylo configuration. Thus, introduction of fluorine in the ribo and xylo configurations affects the conformation of the furanose ring in reciprocal ways. These compounds should provide insight into substrate recognition by Fem transferases and the Ala-tRNA synthetases.

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Conformational analysis of 3′‐fluorinated A(2′‐5′)A(2′‐5′)A fragments

Cited by 17 publications

References 37 publications

Identification of the reaction products of (2′‐5′)oligoadenylate synthetase in the marine sponge

Identification of the reaction products of (2′‐5′)oligoadenylate synthetase in the marine sponge

Synthesis and Application of gem‐Difluoromethylenated and Trifluoromethylated Building Blocks

Synthesis of 3′‐Fluoro‐tRNA Analogues for Exploring Non‐ribosomal Peptide Synthesis in Bacteria

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