Nucleoside derivatives with photolabile protective groups

Details Nucleoside derivatives with photolabile protective groups Nucleoside derivatives with photolabile protective groups

1998-11-16

2000-11-28

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 2531, 536 2533, 536 2534, 536 276, 536 2761, 536 278, 536 2781, 536 285, 536 2852, 536 2853, 536 288, C07H 19052, C07H 19067, C07H 19167, C07H 2100

Patent

active

061537446

ABSTRACT:
The invention relates to nucleo-side derivatives with photo-unstable protective groups of the general formula (I) ##STR1## in which R.sup.1 is H, NO.sub.2, CN, OCH.sub.3, halogen, alkyl or alkoxyalkyl with 1 to 4 C atoms, R.sup.2 is H, OCH.sub.3, R.sup.3 is H, F, Cl, Br, NO.sub.2 or an aliphatic acyl radical with 2 to 5 C atoms, R.sup.4 is H, halogen, OCH.sub.3, an alkyl radical with 1 to 4 C atoms or a possibly substituted aryl radical, R.sup.5 is H or a conventional functional group for producing oligonucleotides, R.sup.6 is H, OH, halogen or XR.sup.8, where X is O or S and R.sup.8 is a conventional protective group in nucleotide chemistry, B is adenine, cytosin, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazol carboxylic acid amid-1-yl or 5-amino-4-imidazol carboxylic acid amide-3-yl, where, if B is adenine, cytosin or guanine, the primary amino function may have a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.

REFERENCES:
Giegrich et al., "New Photo-Labile Protecting Groups in Nucleoside and Nucleotide Chemistry--Synthesis,Cleavage Mechanisms and Applications," Nucleosides & Nucleotides, 17(9-11), 19897-1996 (1998); only abstract supplied.
Pfleiderer et al., "New Protecting Groups in Nucleotide Chemistry," in Biophosphates and Their Analogues-Synthesis, Structure, Metabolism and Activity, pp. 133-142, XP000570661. (Sep. 8, 1986).
Schirmeister et al., "21. Nucleosides," Helvetica Chimica ACTA, vol. 76, No. 1, 1993, pp. 385-401.
Uhlmann et al., "New Improvements in Oligonucleotide Synthesis by Use of the p-Nitrophenylethyl Phosphate Blocking Group and its Deprotection by DBU on DBN," Tetrahedron Letters, vol. 21, pp. 1181-1184, 1980, XP002041323.

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