Nucleoside derivatives with photolabile protective groups

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

C - Chemistry, Metallurgy

07

H

C07H 19/06 (2006.01) C07H 19/04 (2006.01) C07H 19/052 (2006.01) C07H 19/10 (2006.01) C07H 19/16 (2006.01) C07H 19/20 (2006.01) C07H 21/00 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2207912

The invention concerns nucleoside derivatives with photolabile protective groups of general formula (I), in which R1 is H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl with 1 to 4 carbon atoms; R2 is H, OCH3; R3 is H, F, Cl, Br, NO2; R4 is H, halogen, OCH3 or an alkyl group with 1 to 4 carbon atoms; R5 is H or a conventional functional protective group for the oxygen atom, which group is suitable for preparing oligonucleotides; R6 is H, OH, halogen or XR8, wherein X is O or S and R8 is a protective group conventional in nucleotide chemistry; B is adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurine- 9-yl, hypoxanthine-9-yl, 5-methylcytosine-1-yl, 5-amino-4-imidazole carboxylic acid amide-1-yl or 5-amino-4-imidazole carboxylic acid amide-3-yl, wherein, if B is adenine, cytosine or guanine, the primary amino function optionally comprises a permanent protective group. These derivatives can be used for the light-controlled synthesis of oligonucleotides on a DNA chip.

La présente invention concerne des dérivés de nucléosides comportant des groupes protecteurs photolabiles, de formule générale (I) où R?1¿ = H, NO¿2?, CN, OCH¿3?, halogène ou alcoyle ou alcoxyalcoyle ayant de 1 à 4 atomes de C; R?2¿ = H, OCH¿3?; R?3¿ = H, F, Cl, Br, NO¿2?; R?4¿ = H, halogène, OCH¿3? ou un reste d'alcoyle ayant de 1 à 4 atomes de C; R?5¿ = H ou un groupe protecteur fonctionnel usuel pour l'atome d'oxygène, convenant pour la préparation d'oligonucléotides; R?6¿ = H, OH, halogène ou XR?8¿, avec X = 0 ou S et R?8¿ étant un groupe protecteur usuel en chimie des nucléotides; B = adénine, cytosine, guanine, thymine, uracile, 2, 6-diaminopurin-9-yle, hypoxanthin-9-yle, 5-méthylcytosin-1-yle, 5-amino-4-amide d'acide carboxylique imidazol-1-yle ou 5-amino-4-amide d'acide carboxylique imidazol-3-yle. Dans le cas où B = adénine, cytosine ou guanine, la fonction amino primaire comporte, le cas échéant, un groupe protecteur permanent. Ces dérivés peuvent être employés pour la synthèse, commandée par la lumière, d'oligonucléotides sur une plaquette d'ADN.

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