Nucleic Acids Research, 1994, Vol. 22, No. 22 4810-4817
© 1994
CHEMISTRY |
Synthesis and properties of oligodeoxyribonucleotide—polyethylene glycol conjugates
Institute für Organische und Bioorganische Chemie, Humboldt-Universität zu Berlin Hessische Straße 1–2, D–10099 Berlin 1Institute für Biochemie, Freie Universität Berlin Thielallee 63, D–14195 Berlin 2Institute für Medizinische Physik und Biophysik, Westfälische Wilhelmsuniversität Robert-Koch-Straße 31, D–48149 Münster, Germany
*To whom correpsondence should be addressed
Received May 6, 1994. Revised August 23, 1994. Accepted August 23, 1994.
Pools of oligonucleotide conjugates consisting of 10 – 400 different molecular species were synthesized. The conjugates contained a varying number of ethylene glycol units attached to 3'-terminal, 5'-terminal and internal positions of the oligonucleotides. Conjugate synthesis was performed by phosphoramidite solid phase chemistry using suitably protected polyethylene glycol phosphoramidites and PEG-derivatized solid supports containing polydisperse PEGs of various molecular weight ranges. The pools were analyzed and fractionated by chromatographic and electrophoretic techniques, and the composition of isolated conjugates was revealed by matrix-assisted laser desorption/ionization mass spectrometry. The number and attachment sites of coupled ethylene glycol units greatly influence the hydrophobicity of the conjugates, as well as their electrophoretic mobilities. Conjugation had little effect on the hybridization behavior of oligonucleotide conjugates with unmodified complementary oligonucleotide strands. Melting temperatures were between 67 and 73°C, depending on the size and number of coupled PEG chains, compared to 68°C for the unmodified duplex. Conjugates with PEG coupled to both 3'- and 5'-terminal positions showed a more than 10–fold increase in exonuclease stability.
+Present address: Massachusetts Institute of Techonology, Department of Biology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA
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