Nucleosylaminosäuren als Bausteine zur Synthese modifizierter Oligonucleotide

Nucleosyl Amino Acids as Building Blocks for the Synthesis of Modified Oligonucleotides

by Boris Schmidtgall
Doctoral thesis
Date of Examination:2014-05-09
Date of issue:2014-05-13
Advisor:Prof. Dr. Christian Ducho
Referee:Prof. Dr. Christian Ducho
Referee:Prof. Dr. Ulf Diederichsen
Persistent Address: http://dx.doi.org/10.53846/goediss-4502

 

 

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Abstract

English

It has been proposed that biopolymers need to be uniformly charged to form self-sustaining chemical systems. We have therefore established a method for the site-selective replacement of natural phosphodiester linkages of oligonucleotides (ON) by the positively charged NAA (nucleosyl amino acid) motif. The structure of these building blocks was inspired by naturally occurring muraymycin antibiotics. The phosphoramidite reagents were used to prepare various modified DNA-ON by solid phase-supported synthesis. The resultant modified ON were investigated with respect to structural and thermodynamic properties. Melting experiments revealed only a slight decrease in thermal stability of duplices bearing one NAA-modified strand. Further results indicated that mismatch recognition is not harmed and no structural distortions of duplices occur. These results challenge the hypothesis of the uniform charge pattern to be physico-chemically necessary for replicable biopolymers.
Keywords: modified nucleic acids; nucleosides; nucleosyl amino acids
Schlagwörter: Modifizierte Nucleinsäuren; Nucleoside; Nucleosylaminosäuren
 
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