‘Ethylene‐Bis[phosphonate] Nucleic Acids’: Novel Monomeric Synthons for the Solid‐Phase Synthesis of (PCH 2 CH 2 P)‐Bridged Oligonucleotides | Zendy

Farschtschi Nasser | Zendy

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‘Ethylene‐Bis[phosphonate] Nucleic Acids’: Novel Monomeric Synthons for the Solid‐Phase Synthesis of (PCH 2 CH 2 P)‐Bridged Oligonucleotides

Author(s) -

Farschtschi Nasser

Publication year - 2004

Publication title -

chemistry and biodiversity

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.427

H-Index - 70

eISSN - 1612-1880

pISSN - 1612-1872

DOI - 10.1002/cbdv.200490034

Subject(s) - chemistry , synthon , oligonucleotide , nucleic acid , oligonucleotide synthesis , solid phase synthesis , monomer , ethylene , phosphonate , combinatorial chemistry , stereochemistry , cleavage (geology) , catalysis , organic chemistry , dna , polymer , peptide , biochemistry , geotechnical engineering , fracture (geology) , engineering

An efficient synthesis of modified deoxyribonucleosidic building units, containing the ‘ethylene‐bisphosphonate nucleic acids’ (EBPNAs) 1 or 2 , has been developed. By means of solution‐phase incorporation of 11 , the oxidized form of 2 , dinucleotide analogs of type 13 were prepared. The same strategy was used to incorporate 2 into the 5′‐terminal position of the 12‐mer homopolynucleotide methylphosphonate 14 . A preliminary approach for solid‐phase incorporation of the nucleosidic building block 1 into a preselected position of an oligonucleotide sequence to give 19 is presented, a reaction performed by means of a coupling strategy involving catalytic oxazaphospholidine‐ring cleavage.

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