Patent ID: 6531581
Filing Date: 2003-03-11
Classification: C07H

Abstract:
A derivatized pyrimidine or purine compound having the following structure: wherein, L is a linker group selected from the group consisting of â€”CH&boxH;CHâ€”C(O)â€”NHâ€”(CH2)nâ€”NHâ€”, â€”CH&boxH;CHâ€”C(O)â€”NHâ€”CH2â€”CH2(Oâ€”CH2â€”CH2)mâ€”NHâ€”, â€”C Câ€”C(O)â€”(CH2)nâ€”NHâ€”, â€”CH&boxH;CHâ€”C(O)â€”NHâ€”(CH2)nâ€”CO2â€”, â€”CH&boxH;CHâ€”C(O)â€”NHâ€”(CH2)nâ€”NHâ€”, â€”(CH2)nâ€”NHâ€”, and â€”NHâ€”(CH2)nâ€”NHâ€”, wherein n is an integer from 2 to 12, and m is 1 or 2, and Q is a quencher group selected from the group consisting of radicals of azo dyes and triphenyl methane dyes; P represents a pyrimidine selected from the group consisting of uridine, thymidine and cytosine or the purine adenine; substituted with a linker L at the 4 position, when P is a pyrimidine and at the 8 position when P is a purine; wherein said pyrimidine is linked to the sugar at the 1-position nitrogen and said guanine is linked to the sugar at the 9-position nitrogen and either: x is an activated phosphorus group capable of bonding to a 3â€²-hydroxyl group of a nucleotide or polynucleotide selected from the group consisting of HOâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, HOâ€”P(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, HOâ€”Pâ€”(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, (HO)2P(&boxH;S)â€”Oâ€”, (HO)2P(&boxH;O)â€”Oâ€”(HO)P(&boxH;O)â€”Oâ€”(HO)P(&boxH;S)â€”Oâ€”, â€”Oâ€”P(OCH3)(N(iso-propyl)2), â€”Oâ€”P(OCH2CH2CN)(N(isopropyl)2) and â€”Oâ€”P(CH3)(N(iso-propyl)2); or x is NH2, H, OH or a protected hydroxyl; y is a protected hydroxyl group, OH, H or NH2, and z is â€”H, â€”OH, â€”F, â€”OCH3, â€”O-allyl, a protected hydroxyl group, â€”NH2 or a protected amine group; or y is an activated phosphorus group capable of bonding to a 5â€² hydroxyl group of a nucleotide or polynucleotide selected from the group consisting of HOâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, HOâ€”P(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, HOâ€”Pâ€”(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”P(&boxH;O)(â€”OH)â€”Oâ€”, (HO)2P(&boxH;S)â€”Oâ€”, (HO)2P(&boxH;O)â€”Oâ€”(HO)P(&boxH;O)â€”Oâ€”(HO)P(&boxH;S)â€”Oâ€”, â€”Oâ€”P(OCH3)(N(iso-propyl)2), â€”Oâ€”P(OCH2CH2CN)(N(isopropyl)2) and â€”Oâ€”P(CH3)(N(iso-propyl)2); or y is NH2, H, OH or a protected hydroxyl; x is a protected hydroxyl group, OH, H or NH2, and z is â€”H, â€”OH, â€”F, â€”OCH3, â€”O-allyl, a protected hydroxyl group, NH2 or a protected amine group.