- SYNTHESIS OF URIDINE OLIGONUCLEOTIDE BY THE REACTION OF UNPROTECTED URIDINE WITH TRI-(IMIDAZOLYL-(1))PHOSPHINE
-
Uridine oligonucleotide was synthesized by the reaction of unprotected uridine with tri-(imidazolyl-(1))phosphine and the successive oxidation of the resulting phosphite with iodine and water.
- Shimidzu, Takeo,Yamana, Kazushige,Murakami, Akira,Nakamichi, Kikumi
-
-
Read Online
- Uridine Oligonucleotide Synthesis by the Reaction of Uridine with Tri-(imidazol-1-yl)phosphine
-
Uridine oligonucleotides have been synthesized using tri-(imidazol-1-yl)phosphine.The procedure involves two steps: (i) the reaction of uridine with tri-(imidazol-1-yl)phosphine (60 min) and (ii) the in situ oxidation of the resulting phosphite with iodine and water (10 min).Uridine oligonucleotides up to a hexamer were obtained in high yield at a tri-(imidazol-1-yl)phosphine to uridine ratio of 1.5 at -78 deg C.The inter-ribonucleotidic linkage of the oligomer consists of 2'-5'- and 3'-5'-linkages, formed in the oxidation process.Additives such as metal cations and polynucleotides in the oxidation process showed a significant effect on the formation of the internucleotidic linkage.
- Shimidzu, Takeo,Yamana, Kazushige,Nakamichi, Kikumi,Murakami, Akira
-
-
Read Online
- Synthesis of N6,N6-dialkyladenine nucleosides using hexaalkylphosphorus triamides produced in situ
-
Reactions between secondary amines and phosphorus trichloride (PCl 3) leads to the formation of the corresponding tris(dialkylamino) phosphanes or hexaalkylphosphorus triamides [HAPTs: (R2N) 3P]. Treatment of silyl-protected 2′-deoxyinosine and acetyl-protected inosine with the HAPTs produced in situ, together with iodine (I2), leads to the formation of N6,N6- dialkyladenosine and -2′-deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I2 has been studied by 31P{1H} NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Lakshman, Mahesh K.,Choudhury, Asad,Bae, Suyeal,Rochttis, Eliezer,Pradhan, Padmanava,Kumar, Amit
-
experimental part
p. 152 - 159
(2009/07/05)
-
- Preparation of (2?-5?)-oligonucleotides based on 6-N- benzylaminopurineriboside using the Spicaria violacea fungal enzyme complex
-
A method for chemico-enzymatic synthesis of (2?-5?)-oligonucleotides with 6-N-benzylaminopurineriboside as the nucleoside units was proposed. The method consisted of enzymatic hydrolysis of the oligonucleotides with mixed (2?-5?)-(3?-5?)-phosphodiesterbonds that were prepared by polymerization of 6-N-benzyladenosine-2?(3?)-monophosphate by using (3?-5?)-specific nuclease and phosphatase contained in the filtrate of culture medium of the mycelial fungus Spicaria violacea.
- Kulak,Tkachenko,Grishan,Kukharskaya,Eroshevskaya,Kalinichenko,Zinchenko
-
experimental part
p. 74 - 78
(2009/07/18)
-
- Synthetic fragments of antigenic lipophosphoglycans from Leishmania major and Leishmania mexicana and their use for characterisation of the Leishmania elongating α-D-mannopyranosylphosphate transferase
-
The phosphorylated branched heptasaccharides 7 and 8, the octasaccharide 9 and the phosphorylated trisaccharides 5 and 6, which are fragments of the phosphoglycan portion of the surface lipophosphoglycans from Leishmania mexicana (5) or L. major (6-9), we
- Higson, Adrian P.,Ross, Andrew J.,Tsvetkov, Yury E.,Routier, Francoise H.,Sizova, Olga V.,Ferguson, Michael A. J.,Nikolaev, Andrei V.
-
p. 2019 - 2030
(2007/10/03)
-
- Parasite glycoconjugates. Part 9. Synthesis of dec-9-enyl β-D-galactopyranosyl-(1→4)-α-D-mannopyranosyl phosphate and its epimers at the D-galactose moiety, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
-
A set of phosphodisaccharides, substrate analogues, which will be used to study the acceptor substrate specificity of the Leishmania biosynthetic enzymes, have been synthesized using the trichloroacetimidate method for the glycosylation reactions, SN
- Ivanova, Irina A.,Ross, Andrew J.,Ferguson, Michael A. J.,Nikolaev, Andrei V.
-
p. 1743 - 1753
(2007/10/03)
-
- Imidazo-oxazaphosphorines as precursors to chiral phosphite triesters
-
New bicyclic imidazo-oxazaphosphorines underwent a highly diastereoselective displacement of the imidazole moiety upon reaction with various alcohols, leading to chiral phosphite triesters as single diastereomers. The introduction of a nucleoside on this
- Marsault, Eric,Just, George
-
p. 939 - 955
(2007/10/03)
-
- Cyclic Phosphorylation Reaction of Diols with Tri(1-imidazolyl)phosphine
-
Tri(1-imidazolyl)phosphine (1) gave the cyclic phosphite quantitatively in the reactions with the diols possessing favorably placed hydroxyl groups in which the distance between the two oxygen atoms is 2.7-3.0 Angstroem.The both five- and six-membered cyclic phosphites were obtained quantitatively from the reactions of the diols possessing flexible chains with 1.The course of the selective formation of ribonucleoside 2',3'-cyclic 1-imidazolylphosphonite was interpretated by the higher reactivity of 1 toward the 2'- or 3'-hydroxyl group than toward the 5'-hydroxyl group of ribonucleoside.
- Shimidzu, Takeo,Yamana, Kazushige,Kanda, Naoya,Kitagawa, Susumu
-
p. 3483 - 3485
(2007/10/02)
-