Synthesis of oligodeoxynucleoside methylphosphonates utilizing the fert-butylphenoxyacetyl group for exocyclic amine protection | Zendy

Nanda D. Sinha | Zendy; Dennis P. Michaud | Zendy; Saroj K. Roy | Zendy; Ralph Casale | Zendy

Open Access

Synthesis of oligodeoxynucleoside methylphosphonates utilizing the fert-butylphenoxyacetyl group for exocyclic amine protection

Author(s) -

Nanda D. Sinha,

Dennis P. Michaud,

Saroj K. Roy,

Ralph Casale

Publication year - 1994

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/22.15.3119

Subject(s) - biology , group (periodic table) , amine gas treating , organic chemistry , chemistry , environmental engineering , engineering

Oligodeoxynucleoside methylphosphonates were synthesized using methylphosphonamidite monomers incorporating the base labile tert-butylphenoxyacetyl (t-BPA) protecting group on the exocyclic amines of dA, dC, and dG. Synthesis of the oligodeoxynucleoside methylphosphonates required only a small change in oxidation solution from standard DNA synthesis. The increased lability of the t-BPA group over the standard benzoyl and isobutyryl protection permitted the use of milder basic deprotection conditions. Deprotection of the nucleoside bases and release from support was best accomplished by a short treatment with ammonia saturated methanol. This procedure resulted in minimal backgone degradation with no base modifications. Analysis of the resultant oligodeoxynucleoside methylphosphonates by reverse phase HPLC and MALDI-TOF mass spectroscopy are described.

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