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N 7 ‐DNA: Synthesis and Base Pairing of Oligonucleotides Containing N 7 ‐(2‐Deoxy‐β‐ D ‐ erythro ‐pentofuranosyl)guanine ( N 7 G d )
Author(s) -
Seela Frank,
Leonard Peter
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.19960790215
Subject(s) - chemistry , phosphoramidite , guanine , oligonucleotide , nucleobase , phosphodiester bond , stereochemistry , cytosine , deoxyribonucleotide , oligonucleotide synthesis , anomer , diastereomer , thymine , nucleic acid , phosphonate , residue (chemistry) , guanosine , nucleotide , dna , biochemistry , rna , gene
The synthesis of oligonucleotides containing N 7 ‐(2‐deoxy‐β‐ D ‐ erythro ‐pentofuranosyl)guanine ( N 7 G d ; 1 ) is described. Compound 1 was prepared by nucleobase‐anion glycosylation of 2‐amino‐6‐methoxypurine ( 5 ) with 2‐deoxy‐3,5‐di‐ O ‐(4‐toluoyl)‐α‐ D ‐ erythro ‐pentofuranosyl chloride ( 6 ) followed by detoluoylation and displacement of the MeO group ( 8→10→1 ). Upon base protection with the (dimethylamino)methylidene residue (→ 11 ) the 4,4‐dimethoxytrityl group was introduced at OHC(5′) (→ 12 ). The phosphonate 3 and the phosphoramidite 4 were prepared and used in solid‐phase oligonucleotide synthesis. The self‐complementary dodecamer d( N 7 GC) 6 shows sigmoidal melting. The T m of the duplex is 40°. This demonstrates that guanine residues linked via N(7) of purine to the phosphodiester backbone are able to undergo base pairing with cytosine.