Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-10-20
1997-10-14
Kunz, Gary L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 261, 536 268, 536 273, 536 285, 536 2853, 536 243, C07H 1906, C07H 1916, C07H 2100
Patent
active
056774419
ABSTRACT:
Process for the production of oligonucleotides of formula II, in which the exocyclic amino groups of the bases adenine, guanine, cytosine, 7-deazaadenine and 7-deazaguanine carry N-phenylacetyl groups, are used for oligonucleotide synthesis, wherein in a first step a starting nucleotide is bound to a solid carrier, subsequently the desired oligonucleotide is synthesized by stepwise coupling with appropriately activated further monomeric nucleotide building blocks of the general formula I with the above-mentioned meanings, if desired, trivalent phosphorus is oxidized to pentavalent phosphorus during and after the synthesis, the oligonucleotide is cleaved from the carrier and the 5' protecting groups are cleaved off. The phenylacetyl functional groups that protect exocyclic NH.sub.2 groups of the bases can be cleaved off in a mild way with penicillin amidohydrolase (EC 3.5.1.11).
REFERENCES:
H. Waldmann et al., "Selective Enzymatic Deprotection of Hydroxy and Amino Groups in Carbonhydrates and Nucleosides", Jan. 1994 The Entire Document pp. 65-67.
Li et al., Biochemistry, vol. 28, pp. 5779-5786, (1989).
Resse et al., Journal of the Chemical Society, Perkin Trans 1, pp. 1263-1271, (1984).
Brown et al., Journal of the Chemical Society, Perkin Transactions 1, pp. 1751-1767, (1989).
Moon et al. Bulletin of the Korean Chemical Society, vol. 12, pp. 196-199, (1991).
Xu et al., Tetrahedron Letters, vol. 32, pp. 2817-2820, (1991).
B. Chaudhuri et al., Tetrahedron Letters, vol. 25, pp. 4037-4040 (1984).
Dineva et al., Bioorganic and Medicinal Letters, vol. 3, pp. 2781-2784, (1993).
Waldmann et al., Synlett, pp. 65-67, (1994).
Birkner Christian
Heuser Axel
Muehlegger Klaus
Reidel Armin
von der Eltz Herbert
Boehringer Mannheim GmbH
Kunz Gary L.
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