Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1991-04-19
1992-12-29
Nutter, Nathan M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
549499, C07H 1900, C07H 2100, C07D30702
Patent
active
051752662
ABSTRACT:
Nucleoside derivatives which contain a nucleo-base, a sugar and an amino acid backbone of the structure: ##STR1## where R' refers to the various amino acid side chains or their blocked equivalent and R refers to a nucleo-base or its blocked equivalent. The synthesis of these nucleoside derivatives proceeds by a series of steps including oxidation of the 3'-azido nucleoside derivative, coupling to a benzylated ester of an amino acid to yield the amide and hydrogenation. The adenine, guanine, cytosine and thymine nucleosides with an amino acid at the 5' terminus are synthesized. From such monomers oligonucleotides can be synthesized which possess an amino acid backbone, using either solid state phase chemistry or liquid phase chemistry.
REFERENCES:
patent: 4625065 (1986-11-01), Heather
patent: 4736036 (1988-04-01), Mathiaparanam
patent: 4889952 (1989-12-01), Shimizu et al.
Singh et al "Ruthenium Tetraoxide: A Mild Reagent for the Oxidation of 2', 3'-O-Isopropylidene Purine Nucleosides" Tetrahedron Letters 33:237-240 (1992).
Hogan Michael E.
Rao Takkellapati S.
Revankar Ganapathi R.
Varma Rajender S.
Baylor College of Medicine
Nutter Nathan M.
Triplex Pharmaceutical Corporation
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