2 -Deoxy adenosine 5 -monophosphate

When two acid molecules condense by elimination of a molecule of water, the product is called an acid anhydride, as can be seen in Figure 12.60. Acid anhydrides are always very reactive, or high-energy, compounds. When deoxy-adenosine monophosphate forms an anhydride with phosphoric acid, we have deoxyadenosine diphosphate (dADP). Of course, if we add an additional phosphate group, we have deoxyadenosine triphosphate (dATP). 

RaitVK, Zhang Q,Fabris D,et al. Conversions of formaldehyde-modified 2 -deoxy-adenosine 5 -monophosphate in conditions modeling formalin-fixed tissue dehydration. I. Histochem. Cytochem. 2006 54 301-310. 

Fig. 14.1 Cellular pathway of methotrexate. ABCBl, ABCCl-4, ABC transporters ADA, adenosine deaminase ADP, adenosine diphosphate AICAR, aminoimidazole carboxamide ribonucleotide AMP, adenosine monophosphate ATIC, AICAR transformylase ATP, adenosine triphosphate SjlO-CH -THF, 5,10-methylene tetrahydrofolate 5-CHj-THF, 5-methyl tetrahydro-folate DHFR, dihydrofolate reductase dTMP, deoxythymidine monophosphate dUMP, deoxy-uridine monophosphate FAICAR, 10-formyl AICAR FH, dihydrofolate FPGS, folylpolyglutamyl synthase GGH, y-glutamyl hydrolase IMP, inosine monophosphate MTHFR, methylene tetrahydrofolate reductase MTR, methyl tetrahydrofolate reductase MTX-PG, methotrexate polyglutamate RFCl, reduced folate carrier 1 TYMS, thymidylate synthase. Italicized genes have been targets of pharmacogenetic analyses in studies published so far. (Reproduced from ref. 73 by permission of John Wiley and Sons Inc.)...

The acyclic nucleoside phosphonate, 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), also known as Adefovir [1], can be considered as an analogue of (2 -deoxy)adenosine 5 -monophosphate ((d)AMP ) [2]. PMEA has excellent antiviral properties [1] and in the form of its bis(pivaloyloxymethyl)ester, Adefovir dipivoxil, it has recently been approved by the US Food and Drug Administration (FDA) for the treatment [3] of hepatitis B patients these people suffer from an infection of aDNAvirus. 

Nucleotides are named by adding a term denoting the number of phasphate groups (and their position) to the name of the nucleoside e.g. adenosine 5-monophosphate, AMP (or adenylate). In general, nucleotides are assumed to be ribonucleotides unless the prefix deoxy (or d- as abbreviation) is used. (See Figures 20.5 and 20.6)... 

Ca2+j, intracellular calcium cAMP, cyclic adenosine 3, 5 -monophosphate PLC, phospholipase C isoPs, isoprostanes 15d-PGJ2, 15-deoxy-A12,14-PGJ2. 

Chemical Synthesis.—Purine nucleoside 5 -monophosphates enriched with or 0 on the phosphate group are conveniently prepared by treating phosphorus pentachloride in dry triethyl phosphate with one equivalent of the appropriately labelled water to give PO]- or P 0]P0Cl3, which is not isolated but mixed with adenosine or guanosine in the same solvent. Work-up of the resulting 5 -phos-phorodichloridate in similarly labelled water permits the formation of pO]-or P 0]AMP (or GMP) in fair yield with good enrichment. The 5 -monophos-phates of the 5 -C-methyl uridines derived from 6-deoxy-D-allose and 6-deoxy-L-talose have been prepared via phosphorylation of the 2, 3 -0,0-ethoxymethyl-idene derivative of the nucleosides (1) with -cyanoethyl phosphate and DCC or TPS-Cl. The same method has been used to phosphorylate iV -benzoylated 2, 3 -0,C -isopropylidene derivatives of various 5 -C-alkyladenosine species (2) and also 4 -allyladenosine (3) as part of a study in which derivatives of AMP... 

Nucleosides. Nucleotides, and Derivatives.- 2, 3 ,5 -Trl-0 -acetyl-adenosine and -guanosine, 4- -ethyl-thymidlne, N -methyl-2 -deoxyadenoslne, 5-raethoxymethyl-2 -deoxy-urldlne and its 0-D-threo-isomer, 5-fluoroarablnosylcytoslne, the 2 -deoxynucleo-side (17), cls-thymldine 3 ,5 -cyclic methyl phosphonate and the corresponding 3, 5 -cycllc N,N-dlmethylphosphoramldate,a cobalt(II) complex with 2 -deoxyinosine 5 -monophosphate,... 

Generally, UV absorption spectra can be utilized to determine the family to which an unknown base, nucleoside, or nucleotide belongs. Indeed, the chro-mophore of the nucleosides or nucleotides is typical of the purine or pyrimidine structvu-e, with different maximum absorption wavelengths in the adenosine, guanosine, cytosine, or thymidine series. For example, it is possible to differentiate readily the UV absorption spectra of guanosine (G), G-monophosphate (GMP), deoxy GMP (dGMP), G-diphosphate (GDP), and G-triphosphate (GTP), from those of adenosine (A), AMP, dAMP, ADR, and ATP. 

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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