124482-92-4Relevant articles and documents
Synthesis of nucleoside mono-, di-, and triphosphoramidates from solid-phase cyc/osaligenyl phosphitylating reagents
Ahmadibeni, Yousef,Tiwari, Rakesh K.,Sun, Gongqin,Parang, Keykavous
, p. 2157 - 2160 (2009)
Chloromethyl polystyrene resin was reacted with 5-hydroxysalicylaldehyde in the presence of potassium carbonate to afford polymer-bound 2-hydroxybenzaldehyde. Subsequent reduction with borane solution produced polymer-bound 2-hydroxybenzyl alcohol. The re
Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry
Hardacre, Christopher,Huang, Haifeng,James, Stuart L.,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.
supporting information; experimental part, p. 5846 - 5848 (2011/06/26)
Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.
Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase
Ching, Shi Min,Tan, Wan Jun,Chua, Kim Lee,Lam, Yulin
scheme or table, p. 6657 - 6665 (2010/10/21)
Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation.
Selective synthesis of chlorophosphoramidites using ionic liquids
Amigues, Eric J.,Hardacre, Christopher,Keane, Gillian,Migaud, Marie E.,Norman, Sarah E.,Pitner, William R.
experimental part, p. 1391 - 1396 (2010/05/18)
A range of chlorophosphoramidites have been prepared in ionic liquids and compared with material synthesised in molecular solvents. Through the use of ionic liquids as reaction media the moisture sensitivity and impurity issues hampering existing traditio
Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters
Ahmadibeni, Yousef,Parang, Keykavous
, p. 4483 - 4486 (2008/03/12)
(Chemical Equation Presented) Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3′-azido-3′- deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H- tetrazole. Polymer-bound nucleosides underwent oxidation with fert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.
Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides
Ahmadibeni, Yousef,Parang, Keykavous
, p. 5589 - 5592 (2007/10/03)
(Chemical Equation Presented) Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylating and triphosphitylating reagents to yield the corresponding polymer-bound diphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodiphosphates, triphosphates, and trithiotriphosphates with high regioselectivity.
Effect of acridine with various linker arms attached to C5 position of 2'-deoxyuridine on the stability of DNA/DNA and DNA/RNA duplexes
Ozaki, Hiroaki,Ogawa, Yoshinori,Mine, Masayuki,Sawai, Hiroaki
, p. 911 - 923 (2007/10/03)
Acridine-modified oligodeoxyribonudeotides (ODNs) at the C5-position of a 2'-deoxyuridine via different lengths of linker arms were synthesized. Reaction of 5-(N-aminoalkyl)carbamoylmethyl-2'-deoxyuridines with 9- phenoxyacridine gave the acridine-modified 2'-deoxyuridines which were incorporated into ODNs. The duplexes containing the acridine-modified strands and their complementary DNA or RNA were thermally more stable than that containing the unmodified strand. Thermal stability of the duplexes of the modified ODNs varied depending on the length of the linker arms.
Use of the 1-(2-Fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) Protecting Group in the Solid-Phase Synthesis of Oligo- and Poly-ribonucleotides
Rao, M. Vaman,Reese, Colin B.,Schehlmann, Volker,Yu, Pak Sang
, p. 43 - 56 (2007/10/02)
An approach to the solid-phase synthesis of oligo- and poly-ribonucleotides is described.The synthetic strategy involves the use of building blocks in which two acid-labile groups, 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and 9-phenylxanthen-9-yl
Deoxyribonucleoside phosphoramidites in which an aliphatic amino group is attached to the sugar ring and their use for the preparation of oligonucleotides containing aliphatic amino groups
-
, (2008/06/13)
The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permittin
β-CYANOETHYL N,N-DIALKYLAMINO/N-MORPHOLINOMONOCHLORO PHOSPHOAMIDITES, NEW PHOSPHITYLATING AGENTS FACILITATING EASE OF DEPROTECTION AND WORK-UP OF SYNTHESIZED OLIGONUCLEOTIDES
Sinha, N. D.,Biernat, J.,Koester, H.
, p. 5843 - 5846 (2007/10/02)
β-Cyanoethyl monochlorophosphoamidites of the secondary amines N,N-dimethylamine, N,N-diisopropylamine and morpholine have been prepared which showed quantitative phosphitylation of the protected deoxynucleosides.The phosphitylated deoxynucleosides have successfully been used in the formation of internucleotidic bonds. β-Cyanoethyl nucleoside-3'-N,N-diisopropylphosphoamidites have saticfactorily been used for the synthesis of the oligodeoxynucleotide d(CGGTACCG).
