124680-51-9Relevant academic research and scientific papers
METHOD FOR PREPARING 3'-O-AMINO-2'-DEOXYRIBONUCLEOSIDE-5'-TRIPHOSPHATE
-
, (2020/03/23)
The invention relates to a method for preparing 3 ' -O-amino-2' -deoxyribonucleoside-5 ' - triphosphate. It also relates to a solid support functionalized with at least one N- hydroxyphthalimide moiety and uses thereof for protecting 3 '-hydroxy group of a 2'- deoxyribonucleoside during synthesis of a nucleoside or a derivative thereof.
Tailoring peptide-nucleotide conjugates (PNCs) for nucleotide delivery in bacterial cells
De, Swarup,Groaz, Elisabetta,Herdewijn, Piet
, p. 2322 - 2348 (2014/04/17)
The design and synthesis of peptide-2′-deoxythymidine-5′-O- monophosphate conjugates as potential active delivery systems for nucleotides into auxotrophic E. coli strains is presented. A series of oligopeptides were allowed to react with 5′-O-(dibenzylphosphate)-2′-deoxythymidine or its suitably 3′-derivatized analogues to give the relevant peptide-nucleotide adducts, by the formation of a biolabile chemical connection. Using strategies based on the principles of orthogonal protection and activation, rational variations were made to the linker and the peptide moiety in order to tune the metabolic stability of the conjugates.
Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters.
Jung,Toyota
, p. 2624 - 2635 (2007/10/03)
tert-Butyl thymidylate 3 was prepared from thymidine 1 in six steps and 67% overall yield. When the lithium trianion of 3 (prepared by treatment of 3 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping occurs stereoselectively from either the alpha- or beta-face depending on the electrophile (Scheme 1). Deuterioacetic acid in deuteriomethanol affords mainly the alpha-deuterated product (4a/4b = 2.4:1) while all other electrophiles, e.g., phenylselenenyl chloride, allyl bromide, and N-fluorobenzenesulfonimide (NFSI), give predominately (or completely) the products of attack from the beta-face (5bcd/4bcd = 3.7:1 to 100:0). The structures of the products were determined by coupling constant analysis of both the initial compounds and the diols 6bcd prepared by ester reduction and by formation of the acetonides 7bc. The methyl ester of the 3'-epimer of thymidylic acid 9 was also prepared from thymidine 1 in nine steps and 74% overall yield. When the lithium trianion of 9 (prepared by treatment of 9 with excess LDA and then excess tert-butyllithum) is reacted with electrophiles, trapping also occurs stereoselectively with attack on either the alpha- or beta-face depending on the electrophile (Scheme 2). Again, deuterioacetic acid in deuteriomethanol affords mainly the beta-deuterated product (11a/10a = 1.6:1) while all other electrophiles, e.g., phenylselenenyl chloride, methyl iodide, allyl bromide, and NFSI, gave predominately (or completely) the product of attack from the alpha-face (8.7:1 to 100: 0). Again, the structures of the products were determined by coupling constant analysis of both the initial compounds, and the diols 12b-e were prepared by reduction of the ester and by formation of the acetonides 13bcd. A rationale has been developed using molecular mechanics calculations to explain the diastereoselectivity that involves staggered axial attack on the sp(2) carbon opposite to the pseudoaxial alkoxy group in the most stable half-chair conformation of the enolates, as shown in Schemes 3-5.
Synthesis of Furo[2,3-c]pyran-β-D-nucleosides by radical-cyclization and their conformational analysis by 500 MHz 1H-NMR spectroscopy
Xi,Agback,Sandstrom,Chattopadhyaya
, p. 9675 - 9690 (2007/10/02)
Free-radical, generated from the 3'-phenylseleno nucleosides as the radical precursors 2-5, was efficiently trapped intramolecularly by an olefin or alkyne function anchored from the 5'-end by an ether function to give various [3.4.0]-cis-fused furo[2,3-c
