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Warum Pentose‐ und nicht Hexose‐Nucleinsäuren??. Teil II. Oligonucleotide aus 2′,3′‐Dideoxy‐β‐ D ‐glucopyranosyl‐Bausteinen (‘Homo‐DNS’): Herstellung.
Author(s) -
Böhringer Markus,
Roth HansJÖRg,
Hunziker Jürg,
Göbel Michael,
Krishnan Ravichandran,
Giger Alfred,
Schweizer Bernd,
Schreiber Jakob,
Leumann Christian,
Eschenmoser Albert
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750503
Subject(s) - chemistry , oligonucleotide , cytosine , oligonucleotide synthesis , thymine , nucleoside , nucleic acid , dna , guanine , pentose , uracil , hexose , stereochemistry , base pair , nucleotide , combinatorial chemistry , biochemistry , gene , fermentation , enzyme
Why Pentose and Not Hexose Nucleic Acids? Part II . Preparation of Oligonucleotides Containing 2′,3′‐Dideoxy‐β‐ D ‐glucopyranosyl Building Blocks (7) This paper describes the preparation of the 2′,3′‐dideoxy‐β‐ D ‐glucopyranosyl‐( = 2′,3′‐dideoxy‐β‐ D ‐ erythro ‐hexopyranosyl)‐derived nucleosides of the five bases adenine, cytosine, guanine, thymine, and uracil ( = ‘homo‐de‐oxyribonucleosides’) as well as the synthesis of oligonucleotides derived from them. The methods used for both nucleoside and oligonucleotide synthesis closely follow the known methods of synthesis in the corresponding series of natural 2′‐deoxyribonucleosides and oligonucleotides. The efficient methods of automated DNA synthesis proved to be fully applicable to the synthesis of homo‐DNA oligonucleotides, the only change necessary for achieving satisfactory coupling yields being a slight lengthening of the coupling time. Homo‐DNA oligonucleotides with chain lengths of up to twelve nucleoside units were assembled on solid support either manually or on a commercial DNA synthesizer in scales of 0.4 μmol to as much as 200 μmol and were purified by either reversed‐phase or ion‐exchange HPLC to single‐peak purity according to both chromatographic systems (estimated purity > 95%). The choice of the specific base sequences to be synthesized was determined primarily by the constitutional problems of base pairing that emerged from experimental observations made in the course of systematic studies of the pairing properties of homo‐DNA oligonucleotides. About 100 homo‐DNA sequences were prepared for this purpose. Their pairing properties will be described in Part III of this series; the present paper is restricted to the characterization of the purity and constitutional integrity of a few selected (single‐stranded) oligonucleotides by 1 H‐, 31 P‐, and 13 C‐NMR spectroscopy as well as by FAB and time‐of‐flight mass spectroscopy. The English Footnotes to Schemes 1–9, Fig. 1–12 , and Table 1 provide an extension of this summary.