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Nucleic Acid Analogs with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone “Tricyclo-DNA”. Part 1. Preparation of [(5′R,6′R)-2′-deoxy-3′,5′-ethano-5′,6′-methano-β-D-ribofuranosyl]thymine and -adenine, and the corresponding phosphoramidites for oligonucleotide synthesis

✍ Scribed by Ralph Steffans; Christian Leumann

Publisher
John Wiley and Sons
Year
1997
Tongue
German
Weight
1019 KB
Volume
80
Category
Article
ISSN
0018-019X

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✦ Synopsis

In extension of the bicyclo-DNA nomenclature (see , Foornote 3), the name tricyclo-DNA and, correspondingly, tricyclo-deoxynucleosides was chosen to denominate this type of nucleotide and nucleoside analog.

The numbering scheme as depicted in

Fig. f for nucleosides was chosen in order to be able to use the structural descriptors and notions common in natural nucleotide chemistry (an alternative numbering scheme results when 3',5',5'-bridging by a propane-1,2,3-triyl moiety is assumed; see Exper. Part, names of 1,2, 14, 16, 19, and 21). For sugar intermediates 3-11, the systematic IUPAC nomenclature with the numbering scheme depicted in Fig. f was used. ' ) ' )

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