Deoxyadenosine sugar ring

The conformational mobilities of pyrimidine nucleosides in aqueous solution have been investigated by c.d. measurements in the temperature range —100 to -H40 °C changes in the main c.d. band were ascribed to oscillation of the base about the glycosidic bond and to pseudorotation of the sugar ring. The c.d. spectra of uridine, thymidine, 2 -deoxyadenosine, adenosine, and 9-j8-D-arabino-furanosyladenine in aqueous solution have been measured at pH 7 and 2, and the c.d. spectra of benzoyl, 4-nitrobenzoyl, and anisoyl derivatives of adenosine, uridine, and l-jS-D-ribofuranosylbenzimidazole have also been recorded. ... 

A sugar derivative related to the purine nucleosides, namely methyl 5-(adenin-l-yl)-5-deoxy-2,3-0-isopropylidene-j8-D-ribofurano-side, is formed by the reaction of methyl 5-amino-5-deoxy-2,3-0-iso-propylidene-jS-D-ribofuranoside with l-benzyl-5-cyano-4[(ethoxy-methylene)amino]imidazole, followed by removal of the benzyl group. On fusion, this compound rearranges to methyl 5-deoxy-2,3-0-isopropylidene-5-[(purin-6-yl)amino]-/8-D-ribofuranoside, which can also be obtained from the reaction of methyl 5-amino-5-deoxy-2,3-0-isopropylidene-/8-D-ribofuranoside with 6-chloro-9-(tetrahydropyran-2-yl)purine. In the same manner, methyl 5-amino-5-deoxy-2,3-di-0-p-tolylsulfonyl-/3-D-ribofuranoside reacts with 6-chloro-9-(tetrahydro-pyran-2-yl)purine to give methyl 5-deoxy-5-[9-(tetrahydropyran-2-yl)-purin-6-yl]amino-2,3-di-0-p-tolylsulfonyl-j8-D-ribofuranoside. With liquid ammonia, 5 -0-p-tolylsulfonyladenosine gives 5 -amino-5 -deoxyadenosine. On heating in p-dioxane, ring closure to 3,5 -an-hydroadenosine is observed. ... 

These compounds illustrate the structural diversity of carbohydrates. Glucose is the most common simple sugar, whereas cellulose, which comprises wood, piant stems, and grass, is the most common carbohydrate in the piant world. Doxorubicin, an anticancer drug that has a carbohydrate ring as part of its structure, has been used in the treatment of ieukemia, Hodgkin s disease, and cancers of the breast, biadder, and ovaries. 2 -Deoxyadenosine 5 -monophosphate is one of the four nucieotides that form DNA. 

The base plus the sugar group (without the phosphate group) is called a nucleoside. Nucleosides are named from the bases. For example, the nucleoside composed of adenine with jS-D-ribose is called adenosine. The nucleoside composed of adenine with 2-deoxy-j8-D-ribose is called deoxyadenosine. A nucleotide is named by adding monophosphate (or diphosphate or triphosphate) after the nucleoside name. A number with a prime indicates the position of the phosphate group on the ribose ring. Thus, adenosine-5 -monophosphate is a nucleotide composed of adenine, jS-D-ribose, and a phosphate group at the 5 position of jS-D-ribose. 

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