TY - JOUR A1 - Wessig, Pablo A1 - Möllnitz, Kristian A1 - Hübner, Sebastian T1 - A short and efficient route from myo- to neo-inositol N2 - An efficient route from myo- to neo-inositol is described. The key steps of the sequence are oxidation of the hydroxy group at C-5 to the corresponding ketone, followed by a highly (dr = 7.8:1) stereoselective reduction. The route includes nine steps with an overall yield of 51% and is therefore superior to all hitherto reported methods for the preparation of neo-inositol. Y1 - 2010 UR - http://www.thieme-connect.com/ejournals/toc/synlett U6 - https://doi.org/10.1055/s-0029-1220071 SN - 0936-5214 ER - TY - JOUR A1 - Techen, Anne A1 - Czapla, Sylvia A1 - Möllnitz, Kristian A1 - Budach, Dennis B. A1 - Wessig, Pablo A1 - Kumke, Michael Uwe T1 - Synthesis and spectroscopic characterization of fluorophore-labeled oligospiroketal rods JF - Helvetica chimica acta N2 - Fluorescence probes consisting of well-established fluorophores in combination with rigid molecular rods based on spirane-type structures were investigated with respect to their fluorescence properties under different solvent conditions. The attachment of the dyes was accomplished by 1,3-dipolar cycloaddition between alkynes and azides (click' reaction) and is a prime example for a novel class of sensor constructs. Especially, the attachment of two (different) fluorophores on opposite sides of the molecular rods paves the way to new sensor systems with less bulky (compared to the conventional DNA- or protein-based concepts), nevertheless rigid spacer constructs, e.g., for FRET-based sensing applications. A detailed photophysical characterization was performed in MeOH (and in basic H2O/MeOH mixtures) for i) rod constructs containing carboxyfluorescein, ii) rod constructs containing carboxyrhodamine, iii) rod constructs containing both carboxyfluorescein and carboxyrhodamine, and iv) rod constructs containing both pyrene and perylene parts. For each dye (pair), two rod lengths with different numbers of spirane units were synthesized and investigated. The rod constructs were characterized in ensemble as well as single-molecule fluorescence experiments with respect to i) specific roddye and ii) dyedye interactions. In addition to MeOH and MeOH/NaOH, the rod constructs were also investigated in micellar systems, which were chosen as a simplified model for membranes. KW - Molecular rods KW - Forster resonance energy transfer (FRET) KW - Carboxyfluorescein KW - Carboxyrhodamine KW - Pyrene KW - Perylene KW - Fluorescence Y1 - 2013 U6 - https://doi.org/10.1002/hlca.201200616 SN - 0018-019X SN - 1522-2675 VL - 96 IS - 11 SP - 2046 EP - 2067 PB - Wiley-VCH CY - Weinheim ER - TY - THES A1 - Möllnitz, Kristian T1 - Synthese und Untersuchung von molekularen Stäben basierend auf Oligospiroketalen Y1 - 2012 CY - Potsdam ER - TY - JOUR A1 - Wessig, Pablo A1 - Möllnitz, Kristian T1 - Building blocks for oligospiroketal (OSK) rods and evaluation of their influence on rod rigidity JF - The journal of organic chemistry N2 - We report on the synthesis of three new sleeves and their incorporation in OSK rods. The structures of these sleeves are based on neo-inositol, terephthalaldehyde diacetals, and indacene. To quantify the influence of the sleeves on rod rigidity, we applied the worm-like chain (WLC) model on the new rods and found that this approach is rather disappointing. As the chief cause of this result, we assume that the rigidity of typical molecular rods largely exceeds the rigidity of polymers, which were successfully described by the WLC model. Alternatively, we suggest quantifying the rigidity of molecular rods by fitting an empirical function on the end-to-end distance distribution curve obtained by MD simulations. After checking various function types, the Levy-Martin function proved to be most suitable for this purpose. On the basis of this function, we defined the Levy-Martin parameter and suggest using this parameter for the characterization of the rigidity of molecular rods. Y1 - 2012 U6 - https://doi.org/10.1021/jo300266b SN - 0022-3263 VL - 77 IS - 8 SP - 3907 EP - 3920 PB - American Chemical Society CY - Washington ER - TY - JOUR A1 - Nikolaus, Jörg A1 - Czapla, Sylvia A1 - Möllnitz, Kristian A1 - Höfer, Chris T. A1 - Herrmann, Andreas A1 - Wessig, Pablo A1 - Müller, Peter T1 - New molecular rods - Characterization of their interaction with membranes JF - Biochimica et biophysica acta : Biomembranes N2 - Molecular rods are synthetical molecules consisting of a hydrophobic backbone which are functionalized with varying terminal groups. Here, we report on the interaction of a recently described new class of molecular rods with lipid and biological membranes. In order to characterize this interaction, different fluorescently labeled rods were synthesized allowing for the application of fluorescence spectroscopy and microscopy based approaches. Our data show that the rods are incorporated into membranes with a perpendicular orientation to the membrane surface and enrich preferentially in liquid-disordered lipid domains. These characteristics underline that rods can be applied as stable membrane-associated anchors for functionalizing membrane surfaces. KW - Molecular rod KW - Phospholipid KW - Lipid domain KW - Spiro compound Y1 - 2011 U6 - https://doi.org/10.1016/j.bbamem.2011.08.008 SN - 0005-2736 VL - 1808 IS - 12 SP - 2781 EP - 2788 PB - Elsevier CY - Amsterdam ER - TY - JOUR A1 - Wawrzinek, Robert A1 - Wessig, Pablo A1 - Möllnitz, Kristian A1 - Nikolaus, Joerg A1 - Schwarzer, Roland A1 - Müller, Peter A1 - Herrmann, Andreas T1 - DBD dyes as fluorescent probes for sensing lipophilic environments JF - Bioorganic & medicinal chemistry letters : a Tetrahedron publication for rapid dissemination of preliminary communications on all aspects of bioorganic chemistry, medicinal chemistry and related disciplines N2 - Small fluorescent organic molecules based on [1,3]dioxolo[4,5-f][1,3]benzodioxole (DBD) could be used as probes for lipophillic microenvironments in aqueous solutions by indicating the critical micelles concentration of detergents and staining cell organelles. Their fluorescence lifetime decreases drastically by the amount of water in their direct environment. Therefore they are potential probes for fluorescence lifetime imaging microscopy (FLIM). KW - Fluorescence lifetime probes KW - FLIM KW - Cell staining KW - Lysotrackers KW - Detergents Y1 - 2012 U6 - https://doi.org/10.1016/j.bmcl.2012.07.056 SN - 0960-894X VL - 22 IS - 17 SP - 5367 EP - 5371 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Wessig, Pablo A1 - Möllnitz, Kristian A1 - Kelling, Alexandra A1 - Schilde, Uwe T1 - Crystal structure of 1r,2c,3c,4t,5t,6t-1,2,3,4,5,6-hexakis-trimethylsilanyloxy-cyclohexane, C24H60O6Si6 JF - Zeitschrift für Kristallographie : international journal for structural, physical and chemical aspects of crystalline materials ; New crystal structures N2 - C24H60O6Si6, triclinic, P (1) over bar (no. 2), a = 11.307(2) angstrom, b = 12.159(2) angstrom, = 16.576(2) angstrom, alpha = 109.47(1)degrees, beta = 94.64(1)degrees, gamma = 111.65(1)degrees, V = 1942.3 angstrom(3), Z = 2, R-gt(F) = 0.043, wR(ref)(F-2) = 0.118, T = 210 K. Y1 - 2011 U6 - https://doi.org/10.1524/ncrs.2011.0105 SN - 1433-7266 VL - 226 IS - 2 SP - 228 EP - 230 PB - De Gruyter Oldenbourg CY - München ER -