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Search for "queuosine" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of O6-alkylated preQ1 derivatives

  • Laurin Flemmich,
  • Sarah Moreno and
  • Ronald Micura

Beilstein J. Org. Chem. 2021, 17, 2295–2301, doi:10.3762/bjoc.17.147

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  • scaffold. Keywords: deazapurines; heterocycles; pyrrolopyrimidines; queuosine; RNA cofactors; RNA methylation; Introduction Methylated preQ1 has attracted much attention recently because this compound has been found to function as cofactor for the conserved fold of a non-coding RNA, namely the preQ1
  • this end, robust synthetic routes towards O6-alkylated 7-aminomethyl-7-deazaguanines are urgently needed and reported here. Results and Discussion Biological and synthetic background Role of preQ1 in queuosine biosynthesis and gene regulation Queuine (Q base) is a derivative of guanine that is involved
  • in the biosynthetic pathway of the hypermodified tRNA nucleoside queuosine (Q) (Scheme 1) [5]. The core structure of the nucleobase is 7-aminomethyl-7-deazaguanine, a pyrrolo[2,3-d]pyrimidine also termed prequeuosine base (preQ1) [6][7]. In many bacteria, preQ1 binds to specific mRNA domains and
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Published 02 Sep 2021

Syntheses of 15N-labeled pre-queuosine nucleobase derivatives

  • Jasmin Levic and
  • Ronald Micura

Beilstein J. Org. Chem. 2014, 10, 1914–1918, doi:10.3762/bjoc.10.199

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  • Jasmin Levic Ronald Micura Institute of Organic Chemistry, University of Innsbruck and Center for Molecular Biosciences Innsbruck, Innrain 80–82, 6020 Innsbruck, Austria 10.3762/bjoc.10.199 Abstract Pre-queuosine or queuine (preQ1) is a guanine derivative that is involved in the biosynthetic
  • pathway of the hypermodified tRNA nucleoside queuosine (Que). The core structure of preQ1 is represented by 7-(aminomethyl)-7-deazaguanine (preQ1 base). Here, we report the synthesis of three preQ1 base derivatives with complementary 15N-labeling patterns, utilizing [15N]-KCN, [15N]-phthalimide, and [15N3
  • ]-guanidine as cost-affordable 15N sources. Such derivatives are required to explore the binding process of the preQ1 base to RNA targets using advanced NMR spectroscopic methods. PreQ1 base specifically binds to bacterial mRNA domains and thereby regulates genes that are required for queuosine biosynthesis
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Published 18 Aug 2014

Stereoselective synthesis of carbocyclic analogues of the nucleoside Q precursor (PreQ0)

  • Sabin Llona-Minguez and
  • Simon P. Mackay

Beilstein J. Org. Chem. 2014, 10, 1333–1338, doi:10.3762/bjoc.10.135

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  • pharmacological profiles including antibacterial, antiviral and anticancer properties [2][3][4]. Nucleoside Q precursor (PreQ0) 1 is a common precursor in the biosynthesis of queuosine (Q, 2) and archaeosine (G+, 3), two hyper-modified nucleosides present in the tRNA of prokaryote/eukaryote and euryarchaeota
  • the subject of extensive study [1] and several syntheses of the PreQ0 base or ribonucleoside [9][10][11][12][13][14][15][16] and queuosine [17] have been reported in the literature. Despite this long-lasting interest, examples of purine-based nucleosides containing a sugar or carbosugar motif at the 4
  • subsequently deprotected in a one-pot fashion. Pharmacological assessment of these novel PreQ0 derivatives is currently underway in a variety of kinase-inhibitory studies and will be reported in due course. Biosynthetic pathway leading to nucleosides queuosine and archaeosine. Chemical structure of
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Published 11 Jun 2014
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