- New photolabile protecting groups of the 2-(2- nitrophenyl)ethoxycarbonyl-and the 2-(2-nitrophenyl)ethylsulfonyl-type for the oligonucleotide synthesis
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New photolabile blocking groups have been synthesized and introduced into the 5'-OH position of thymidine. The 5'-O-protected thymidines were irradiated at 365 nm under identical conditions and the half-lives and thymidine yields were determined to investigate the influence of different substituents in the two corresponding series.
- Buehler,Giegrich,Pfleiderer
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p. 1281 - 1283
(2007/10/03)
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- Nucleoside derivatives with photolabile protective groups
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The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) STR1 in which R1 =H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R2 =H, OCH3 R3 =H, F, Cl, Br, NO2 R4 =H, halogen, OCH3, or an alkyl radical having 1 to 4 C atoms R5 =H or a usual functional group for preparing oligonucleotides R6 =H, OH, halogen or XR8, where X=O or S and R8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.
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- New photolabile protecting groups in nucleoside and nucleotide chemistry - Synthesis, cleavage mechanisms and applications
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New photolabile protecting groups have been found in the 2-(2- nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. β-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced β-elimination process is proposed.
- Giegrich,Eisele-Buehler,Hermann,Kvasyuk,Charubala,Pfleiderer
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p. 1987 - 1996
(2007/10/03)
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