Nucleoterpenes of Thymidine and 2′‐Deoxyinosine: Synthons for a Biomimetic Lipophilization of Oligonucleotides. Issue 1 (22nd January 2013)

• Record Type: Journal Article
• Authors: Köstler, Karl; Werz, Emma; Malecki, Edith; Montilla‐Martinez, Malayko; Rosemeyer, Helmut
• Is Part Of: Chemistry & biodiversity. Volume 10:Issue 1(2013:Jan.)
• Page Start: 39
• Page End: 61
• Publication Date: 2013-01-22
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201100338
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>2′‐Deoxyinosine (<bold>1</bold>) and thymidine (<bold>7</bold>) were <italic>N</italic>‐alkylated with geranyl and farnesyl moieties. These hydrophobic derivatives, <bold>3a</bold> and <bold>3b</bold>, and <bold>9a</bold> and <bold>9b</bold>, respectively, represent the first synthetic biomimetic nucleoterpenes and were subsequently 5′‐protected and converted into the corresponding 3′‐<italic>O</italic>‐phosphoramidites, <bold>5a</bold> and <bold>5b</bold> and <bold>11a</bold> and <bold>11b</bold>, respectively. The latter were used to prepare a series of lipophilized oligonucleotide dodecamers, a part of which were additionally labelled with indocarbocyanine fluorescent dyes (Cy3 or Cy5), <bold>18</bold>–<bold>23</bold>. The insertion of the lipooligonucleotides into, as well as duplex formation at artificial lipid bilayers was studied by single‐molecule fluorescence spectroscopy and fluorescence microscopy.</p> </abstract>