Adenosine preparation

As described in U.S. Patent 3,049,536, inosine may be prepared starting with adenosine. 

Fig. 33. Stepwise preparative desorption chromatography of phosphoric esters of adenosine on CS-AV-17 cellosorbent 1) adenine, 2) adenosine, 3) adenosine monophosphate, 4) adenosine diphosphate, 5) adenosine triphosphate...

The Merck compound MK-0608 is a 2 -C-Me-7-deaza-adenosine analog, which has recently been reported to show a 5.7 log drop in viral load in HCV-infected chimpanzees after dosing QD at 2mg/kg (Olsen 2006). An efQcient and practical process for preparing kilogram quantities has been described (Bio et al. 2004). The 12-step synthesis provides an impressive 35% overall yield and starts from the inexpensive diacetone-D-glucose. The synthesis features a novel acyl migration in route to prepare the key crystalline furanose diol intermediate (Fig. 5). The conditions... 

Luciferase assay. In this technique, firefly luciferase is used to measure small amounts of adenosine triphosphate (ATP) in a bacterial culture, ATP levels being reduced by the inhibitory action of aminoglycoside antibiotics. This method may find more application in the future as more active and reliable luciferase preparations become available. 

Catalysis by flavoenzymes has been reviewed and various analogues of FAD have been prepared e.g. P -adenosine-P -riboflavin triphosphate and flavin-nicotinamide dinucleotide ) which show little enzymic activity. The kinetic constants of the interaction between nicotinamide-4-methyl-5-acetylimidazole dinucleotide (39) and lactic dehydrogenase suggest the presence of an anionic group near the adenine residue at the coenzyme binding site of the enzyme. ... 

By this method adenosine triphosphate (ATP) and inosine triphosphate (ITP) were prepared in 89% and 93% yield, respectively 51]... 

Reaction of adenosine analogues with DMAD in acetic acid results in the formation of oxopyrimidopurine esters, 477 (Equation 205). The isomeric compounds, 479, can be prepared from the intramolecular cyclization of... 

The general scheme for preparation of the alkylated adenosine and deoxyadenosine involved the interaction of the appropriate amino-hydrocarbon with a 6-chloropurine riboside (116). This allowed for the most specific interaction without too many byproducts. The molecular structures determined from diffraction studies are shown in Figures 24 and 25. In Figure 24 the shape of an alkylated nucleoside (115) is compared with that of the unalkylated form,... 

The bearing which these discoveries have had on the elucidation of the structure of ribopolynucleotides will be discussed later. It is important to stress here, however, that, for most purposes, the older methods of preparing nucleotides have been superseded by procedures which yield separate isomers of each. Of the techniques mentioned above, paper chromatography iB mainly of analytical value, and is the most convenient method for the qualitative detection of isomeric adenylic acids. The only disadvantage of this method is that the isomers are not completely separable from muscle adenylic acid. The presence of the latter, however, can be readily detected by hydrolyzing it to adenosine by means of the specific 5-nucleotidase present in snake venoms,66 or by deamination by a specific enzyme... 

Van Muijlwijk-Koezen and co-workers utilized the reaction sequence beginning with the deprotonation of aminonitrile 139, which when trapped with various nitriles produced aminoquinazolines 140 upon acid-promoted cyclization, in their preparation of numerous aminoquinazoline as antagonists for the human adenosine A3 receptor <00JMC2227>. 

Fig. 1. Bridging ligands employed in the original platinblau compounds prepared from the reaction of c/s-PtCl2(RCN)2 or K2PtCl4 with these ligands. Arrows show the most likely coordination atoms bridging two platinum atoms. The bridging modes of both cytidine and adenosine are assumed to have the same bridging mode as cytosine in Fig. 3. Numbers in parentheses correspond to the references.

Tipson devoted most of his years in Levene s laboratory accomplishing seminal work on the components of nucleic acids. To determine the ring forms of the ribose component of the ribonucleosides he applied Haworth s methylation technique and established the furanoid structure for the sugar in adenosine, guanosine, uridine, and thymidine. He showed that formation of a monotrityl ether is not a reliable proof for the presence of a primary alcohol group in a nucleoside, whereas a tosyl ester that is readily displaced by iodide affords clear evidence that the ester is at the 5-position of the pentofuranose. Acetonation of ribonucleosides was shown to give the 2, 3 -C -isopropyl-idene derivatives, which were to become extensively used in nucleoside and nucleotide chemistry, and were utilized by Tipson in the first chemical preparation of a ribonucleotide, inosinic acid. 

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