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Xylose‐DNA Containing the Four Natural Bases
Author(s) -
Seela Frank,
Heckel Maximilian,
Rosemeyer Helmut
Publication year - 1996
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.19960790518
Subject(s) - chemistry , phosphoramidite , guanine , oligonucleotide , duplex (building) , stereochemistry , aldose , xylose , phosphonate , aldimine , dna , nucleotide , organic chemistry , catalysis , biochemistry , gene , glycoside , fermentation
Oligonucleotides containing (2′‐deoxy‐β‐ D ‐xylofuranosyl)guanine have been prepared. For this purpose 2‐aminoadenosine ( 5 ) was synthesized and converted to 2′‐deoxy‐β‐ D ‐xyloguanosine ( 1 ). The related 2′‐deoxy‐β‐ D ‐xyloisoguanosine ( 3 ) and 2′‐deoxy‐β‐ D ‐xyloxanthosine ( 4 ) were also synthesized. Compound 1 was converted to the phosphonate and phosphoramidite building blocks 10 and 11 , respectively. The oligodeoxynucleotide (5′‐3′)d(xG‐xT‐xA‐xG‐xA‐xA‐xT‐xT‐xC‐xT‐xA‐xC‐T) ( 18 ) formed a duplex with the same T m as the parent (5′‐3′)‐(G‐T‐A‐G‐A‐A‐T‐T‐C‐T‐A‐C) ( 19 ), but with an inverted CD spectrum.