Gram-scale chemical synthesis of 2'-deoxynucleoside-5'-o-triphosphates.
A simple, straightforward, reliable, and efficient method for the chemical synthesis of sodium salt of 2'-deoxynucleoside-5'-O-triphosphates (dNTPs), starting from the corresponding nucleoside, is described. This improved "one-pot, three-step" synthetic strategy involves the monophosphorylation of nucleoside, followed by reaction with tributylammonium pyrophosphate and hydrolysis of the resulting cyclic intermediate to provide the corresponding dNTP in good yields (65% to 70%). It is noteworthy that the protocol holds good for both the purine deoxynucleotides, such as 2'-deoxyguanosine-5'-O-triphosphate (dGTP) and 2'-deoxyadenosine-5'-O-triphosphate (dATP), and pyrimidine deoxynucleotides, such as 2'-deoxycytidine-5'-O-triphosphate (dCTP), thymidine-5'-O-triphosphate (TTP), and 2'-deoxyuridine-5'-O-triphosphate (dUTP).
Bioorganic Chemistry Division, Life Technologies Corporation, Austin, Texas, USA.
Anilkumar R
AR
Kore
Muthian
M
Shanmugasundaram
Annamalai
A
Senthilvelan
Balasubramanian
B
Srinivasan
D003838:Deoxyadenine Nucleotides / Q000138:chemical synthesis; D003845:Deoxycytosine Nucleotides / Q000138:chemical synthesis; D011756:Diphosphates / Q000737:chemistry; D006868:Hydrolysis; D009705:Nucleosides / Q000737:chemistry; D011685:Purine Nucleotides / Q000138:chemical synthesis*; D011742:Pyrimidine Nucleotides / Q000138:chemical synthesis*; D013942:Thymine Nucleotides / Q000138:chemical synthesis
D003838:Deoxyadenine Nucleotides; D003845:Deoxycytosine Nucleotides; D011756:Diphosphates; D009705:Nucleosides; D011685:Purine Nucleotides; D011742:Pyrimidine Nucleotides; D013942:Thymine Nucleotides; C024107:2'-deoxycytidine 5'-triphosphate; C107241:diphosphoric acid; C026600:2'-deoxyadenosine triphosphate; C024157:thymidine 5'-triphosphate