191474-13-2Relevant articles and documents
Synthesis of C3′ modified nucleosides for selective generation of the C3′-deoxy-3′-thymidinyl radical: A proposed intermediate in LEE induced DNA damage
Audat, Suaad A. S.,Trzasko Love, Cherylann,Al-Oudat, Buthina A. S.,Bryant-Friedrich, Amanda C.
scheme or table, p. 3829 - 3837 (2012/06/29)
DNA damage pathways induced by low-energy electrons (LEEs) are believed to involve the formation of 2-deoxyribose radicals. These radicals, formed at the C3′ and C5′ positions of nucleotides, are the result of cleavage of the C-O phosphodiester bond throu
Technetium-99m-labeling and synthesis of thymidine analogs: Potential candidates for tumor imaging
Teng, Bao,Bai, Yunpeng,Chang, Yu,Chen, Shizhen,Li, Zhaolong
, p. 3440 - 3444 (2008/02/10)
The technetium-99m-labeling and synthesis of a series of thymidine analogs were studied. The target molecules were obtained by using 6-hydrazinopyridine-3-carboxylic acid (HYNIC) as a bifunctional coupling agent and using N-(2-hydroxy-1,1-bis(hydroxymethyl)ethyl)glycine (tricine) and ethylenediamine-N,N′-diacetic acid (EDDA) as coligands. The effects of different spacers between thymidine analog with HYNIC on radiochemical yield were also studied.
Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides
Rejman, Dominik,Masojidkova, Milena,Rosenberg, Ivan
, p. 1683 - 1705 (2007/10/03)
An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.
Study on reactivity and protection of the α-hydroxyphosphonate moiety in 5′-nucleotide analogues: Formation of the 3′-O-P-C(OH)-C4′ internucleotide linkage
Kralikova, Sarka,Masojidkova, Milena,Budesinsky, Milos,Rosenberg, Ivan
, p. 329 - 347 (2007/10/03)
The recently described epimeric nucleosidyl-5′-C-phosphonates (α-hydroxyphos-phonates) represent novel nucleotide analogues that can be incorporated into chimeric oligonucleotides by the phosphotriester condensation method. In order to prepare suitable protected monomer(s) we have studied condensation reaction between protected 2′-deoxythymidine and 2′-deoxythymidinyl-5′-C-phosphonate, both as model compounds, in dependence on the nature of the 5′-hydroxyl protecting group. We have found that the O-acetyl group is unstable in the presence of TPSCl or MSNT used as condensing agents for activation of the phosphorus moiety. This instability negatively influences the scope of the condensation process. On the other hand, introduction of the O-methoxycarbonyl group gave excellent results. The O-methoxycarbonyl group does not participate in the condensation process, and its quantitative introduction into the nucleotide analogues is accomplished using a novel acylating agent, methoxycarbonyl tetrazole.
Synthesis and application of 3′-amino-dye-terminators for dna sequencing
Wojczcwski,Faulstich,Engels
, p. 751 - 754 (2007/10/03)
The synthesis of 3′-aminomodified nucleoside 5′-triphosphates and their coupling with oligoaminoacid-linked dyes is described. Application for DNA dye-terminator sequencing was investigated. Copyright 1997 by Marcel Dekker, Inc.
PHOSPHORAMIDITES AS SYNTHONS FOR POLYNUCLEOTIDE SYNTHESIS
Caruthers, Marvin H.,Brill, Wolfgang,Dellinger, Douglas J.
, p. 549 - 554 (2007/10/02)
Methods for the rapid synthesis of DNA and RNA are described.The procedures involve using nucleoside phosphoramidites as synthons and silica as a polymeric support.Additionally, a novel reaction involving nucleoside O-alkyl methylphosphonothioates is described.
