SYNTHESIS OF DINUCLEOTIDES CONTAINING A BRIDGED NONCHIRAL INTERNUCLEOTIDE 5'-PHOSPHORAMIDATE OR 3'-PHOSPHORAMIDATE LINKAGE

The synthesis of several dinucleoside phosphate derivatives which are linked by phosphoramidate bands [3'-O-P(=O)(O)-NH-5' or 3'-NH-P(=O)(O)-O-5'] has been accomplished. The internucleoside phosphoramidate linkage was performed using the Staudinger reaction which is directly foll...

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Bibliographic Details
Published inTetrahedron Vol. 50; no. 34; pp. 10225 - 10234
Main Authors MAG, M, ENGELS, JW
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 22.08.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOSPHOROTHIOATES
SOLID-PHASE SYNTHESIS
ANALOGS
DNA
PHOSPHORAMIDATE BONDS
SELECTIVE CLEAVAGE
OLIGODEOXYNUCLEOTIDE
OLIGODEOXYRIBONUCLEOTIDES
NUCLEIC-ACIDS
OLIGONUCLEOTIDES
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Summary:The synthesis of several dinucleoside phosphate derivatives which are linked by phosphoramidate bands [3'-O-P(=O)(O)-NH-5' or 3'-NH-P(=O)(O)-O-5'] has been accomplished. The internucleoside phosphoramidate linkage was performed using the Staudinger reaction which is directly followed by a Michaelis-Arbuzov type transformation. Due to the exclusive use of base labile blocking groups deprotection could be carried out very easily in a single step by treatment with concentrated ammonia for 24 hours at 55 degrees C.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)81755-5