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Search for "benzimidazole" in Full Text gives 101 result(s) in Beilstein Journal of Organic Chemistry.

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(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

José L. Jiménez Blanco,
Fernando Ortega-Caballero,
Carmen Ortiz Mellet and
José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

specifically to the minor groove of the DNA. A pentameric thymidyl DNG incorporating bis-benzimidazole (Hoechst 33258) ligand (64) was synthesised [105]. The stability of DNG-Hoechst conjugates 64 and 65 with a 30-mer double-strand DNA (dsDNA) and single-strand DNA (ssDNA) were evaluated. Fluorescent emission

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Graphical Abstract

Figure 1: Schematic representation of sugar aminoacids (SAAs) and (pseudo)amide oligosaccharide mimetics.

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Figure 2: Natural SAAs structures and natural nucleosidic antibiotics.

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Scheme 1: Synthetic route to the target amide-linked sialooligomers. (a) Fmoc-Cl, NaHCO₃, H₂O, dioxane, 0 °C....

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Figure 3: The general structure of glycoamino acids and their corresponding oligomers.

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Figure 4: Conformational analysis of the β(1→2)-amide-linked glucooligomer 9.

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Figure 5: Short oligomeric chains of C-glycosyl D-arabino THF amino acid oligomers.

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Figure 6: (A) Stereoview of the minimized structure of compound 16 (produced by a 500 ps simulation) that mos...

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Figure 7: Structures of linear oxetane-β- and δ-SAA homo-oligomers 19–20.

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Figure 8: 10-Membered ring H-bonds in compound 21 consistent with NMR and modelling investigations.

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Figure 9: General structure of carbopeptoid-oligonucleotide conjugates.

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Figure 10: Protected derivatives of 2,6-diamino-2,6-dideoxy-β-D-glucopyranosyl carboxylic acid 22 and 23.

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Figure 11: Cyclic homo-oligomers containing glucopyranoid-SAAs.

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Scheme 2: Strategy for solid-phase synthesis of cyclic trimers and tetramers containing pyranoid δ-SAAs.

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Figure 12: Cyclic tetramers of L-rhamno- and D-gulo-configured oxetane-SAAs.

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Figure 13: Aminoglycosidic antibiotics of the glycocinnamoylspermidine family.

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Scheme 3: Synthesis of (thio)trehazoline, via triflate, from β-hydroxy(thio)urea.

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Figure 14: Approaches to access pseudoamide-type oligosaccharide mimics.

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Figure 15: Calystegine B₂ analogues 38 and 39 with urea-linked disaccharide structure.

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Figure 16: Rotameric equilibrium shift of 40 by formation of a bidentate hydrogen bond.

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Figure 17: Nucleotide analogues with thiourea and S-methylisothiouronium linkers.

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Scheme 4: Retrosynthetic approach to synthesize thiourea-linked glycooligomers.

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Figure 18: Rotameric equilibria for β-(1→6)-thiourea-linked glucodimer 41.

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Figure 19: Schematic representation of (a) cyclodextrin (CDs) and (b) cyclotrehalan (CTs) family members.

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Scheme 5: Synthesis of guanidine-linked pseudodisaccharides via carbodiimide.

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Figure 20: β(1→6)-Guanidine-linked pseudodi- and pseudotrisaccharides 47 and 48.

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Scheme 6: Synthesis of N-benzylguanidine-linked CT2 50.

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Figure 21: Structure of RNG and DNG.

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Figure 22: Preparation of Fmoc-guanidinium derivatives.

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Figure 23: Structures of the homo-oligomeric RNG derivatives 51–55.

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Figure 24: Phosphoramidite building block 56.

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Figure 25: Structures of DNGs 57–65.

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Figure 26: Structure of the phosphoramidite building block 66.

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Review

Published 22 Feb 2010

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