Nucleoside derivatives with photoliable protective groups

Details Nucleoside derivatives with photoliable protective groups Nucleoside derivatives with photoliable protective groups

C - Chemistry, Metallurgy

07

H

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

Patent

CA 2254065

The invention relates to nucleoside derivatives with photo-unstable protective groups of the general formula (I) in which R1 is H, NO2, CN, OCH3, halogen, alkyl or alkoxyalkyl with 1 to 4 C atoms, R2 is H, OCH3, R3 is H, F, Cl, Br, NO2 or an aliphatic acyl radical with 2 to 5 C atoms, R4 is H, halogen, OCH3, an alkyl radical with 1 to 4 C atoms or a possibly substituted aryl radical, R5 is H or a conventional functional group for producing oligonucleotides, R6 is H, OH, halogen or XR8, where X is O or S and R8 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.

L'invention concerne des dérivés nucléosidiques à groupes protecteurs photolabiles de la formule générale (I) dans laquelle R?1¿ est H, NO¿2?, CN, OCH¿3?, halogène, alkyle ou bien alcoxyalkyle avec 1 à 4 atomes de C, R?2¿ est H, OCH¿3?, R?3¿ est H, F, Cl, Br, NO¿2? ou un radical acyle aliphatique avec 2 à 5 atomes de C, R?4¿ est H, halogène, OCH¿3?, un radical alkyle avec 1 à 4 atomes de C ou bien un radical aryle éventuellement substitué, R?5¿ est H ou un groupe fonctionnel usuel pour la production d'oligonucléotides, R?6¿ est H, OH, halogène ou bien XR?8¿ où X est O ou S et R?8¿ est un groupe protecteur usuel dans la chimie des nucléotides, B est adénine, cytosine, guanine, thymine, uracile, 2,6-diaminopurin-9-yle, hypoxanthin-9-yle, 5-méthylcytosin-1-yle, amid-1-yle d'acide 5-amino-4-imidazolcarboxylique ou bien amid-3-yle d'acide 5-amino-4-imidazolcarboxylique, et si B est adénine, cytosine ou guanine, la fonction amino primaire peut présenter un groupe protecteur permanent. Ces dérivés peuvent s'utiliser pour la synthèse photorégulée d'oligonucléotides sur une plaquette d'ADN.

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