D-Ribose 5-monophosphate

Massoud SS, Sigel H (1988) Metal coordinating properties of pyiimidine-nucleoside-5-monophosphates (CMP, UMP, TMP) and of simple phosphate monoesters, including D-ribose 5-monophosphate. Establishment of relations between complex stability and phosphate basicity. Inorg Chem 27 1447-1453... 

R-PO3 ) (O) 4-nitrophenyl phosphate (NPhp ), phenyl phosphate (php ), uridine S -monophosphate (UMp ), D-ribose 5-monophosphate (RibMp ), thymidine [-l-(2-deoxy-13-D-ribofuranosyl)thymine] 5 -monophosphate (dTMP ), n-butyl phosphate (Bup ), methanephosphonate (MeP ) and ethanephosphonate (EtP ) (from left to right). The least-squares lines (eq. (11)) are drawn through the corresponding 8 data sets (O) taken from ref [38] for the phosphate monoesters and from ref [5] for the phosphonates. The points due to the equilibrium constants for the M VPA systems are based on the values listed In Tables (column 4) and 2 (columns 4 or S). The vertical broken lines emphasize the stability differences from the reference lines they equal log as defined In eq. (12) for the M(PA) complexes. All the plotted equilibrium constants refer to... 

Figure 34-2 illustrates the intermediates and reactions for conversion of a-D-ribose 5-phosphate to inosine monophosphate (IMP). Separate branches then lead to AMP and GMP (Figure 34-3). Subsequent phosphoryl transfer from ATP converts AMP and GMP to ADP and GDP. Conversion of GDP to GTP involves a second phosphoryl transfer from ATP, whereas conversion of ADP to ATP is achieved primarily by oxidative phosphorylation (see Chapter 12).

This enzyme [EC 3.6.1.6] catalyzes the hydrolysis of a nucleoside diphosphate to produce a nucleotide (that is, a nucleoside monophosphate) and orthophosphate. NDP substrates include IDP, GDP, UDP, as well as d-ribose 5-diphosphate. 

In 1932 Levene and Harris128 showed that the hydrolysis of xanthylic acid gave rise to the formation of a D-ribose phosphate which was not identical with the known D-ribose 5-phosphate. Since xanthylic acid is the monophosphate derivative of a ribofuranoside of xanthine it followed that the new phosphate was either D-ribose 2-phosphate or the 3-isomer (L). Shortly thereafter the same authors129 succeeded in reducing the new D-ribose phosphate with hydrogen in the presence of platinum oxide to a ribitol phosphoric acid (LI) which was completely... 

Bookser, B. C., Kasibhatla, S. R., Erion, M. D. AMP deaminase inhibitors. 4. Further N3-substituted coformycin aglycon analogues N3-alkylmalonates as ribose 5 -monophosphate mimetics. J. Med. Chem. 2000, 45(8), 1519-1524. 

The substrate for this reaction, ct-D-ribose-5-phosphate, is a product of the pentose phosphate pathway.) Figure 14.24 illustrates the initial phase in the pathway by which PRPP is converted to inosine monophosphate (inosinate), the first purine nucleotide. The process begins with the displacement of the pyrophosphate group of PRPP by the amide nitrogen of glutamine in a reaction catalyzed by glutamine PRPP amidotransferase. This reaction is the committed step in purine synthesis. The product formed is 5-phospho-/3-D-ribosylamine. 

It has now been found that the ADP-ribose moiety of nicotinamide adenine dinucleotide is also transferred onto some pro-teins. " When histone serves as an acceptor, several ADP-ribose units are transferred in succession, so that a short chain of oligo-(ADP-ribose), linked covalently to the protein, is formed. In another reaction, transferase II, a soluble enzyme involved in protein synthesis in mammalian cells, acts as an acceptor of a single ADP-ribose unit in the presence of diphtheria toxin. - Treatment of the product with venom pyrophosphatase releases adenosine 5 -monophosphate, but the D-ribose 5-phosphate portion still remains attached to the protein it is, therefore, assumed that the linkage involves C-1 of D-ribose. The transferase II that carries the ADP-ribose unit is completely inactive, but it can be reactivated by incubating with nicotinamide and diphtheria toxin. Under these conditions, the reaction is reversed, generating free transferase II protein and nicotinamide adenine dinucleotide. Thus, diphtheria toxin was shown to have a very specific transglycosylase activity the mechanism of this reaction has been studied in detail. ... 

Compound 3 was prepared from commercially available (/ )-(- -)-5-hy-droxymethyl-5H-furan-2-one by 0-benzylation and subsequent conjugate addition of (PhMe2Si)2 Cu(CN)Li2, and converted to 2-deoxy-L-ribose (5) via the 2-deoxy-L-ribonolactone derivative 4 2 -Deoxy-D-ribose 5-phosphates Relabelled at C-3 and C-4, and/or at C-5, were prepared in a chemoenz3miatic approach by cyclizing appropriately labelled dihydroxyacetone monophosphates with unlabelled acetaldehyde. By use of [ 2]-, or [2- RC]-... 

Evidence from a number of sources indicated that pentose phosphates were metabolized in a series of reactions that resulted in the formation of hexose monophosphates and hexose diphosphates. Several enzyme steps are involved in these transformations. The reaction between D-ribulose 5-phosphate and D-ribose 5-phosphate to form D-sedoheptulose 7-phosphate and D-glyceraldehyde 3-phosphate is catalyzed by an enzyme known as transketolase (91). This enzyme is found in plant, animal, and bacterial cells. Thiamine pyrophosphate (TPP) and Mg ions are required as cofactors. The mechanism of the reaction was suggested (92) as shown in reaction (28). 

Posttranslational modification of preformed polynucleotides can generate additional bases such as pseudouridine, in which D-ribose is linked to C-5 of uracil by a carbon-to-carbon bond rather than by a P-N-glycosidic bond. The nucleotide pseudouridylic acid T arises by rearrangement of UMP of a preformed tRNA. Similarly, methylation by S-adenosylmethionine of a UMP of preformed tRNA forms TMP (thymidine monophosphate), which contains ribose rather than de-oxyribose. 

The results indicated a specific conversion of C-6 of D-glucose into C-5 of D-ribose, explicable by the hexose monophosphate pathway, and suggested conversion of C-l of 2-amino-2-deoxy-D-glucose into C-l of D-ribose, which could be explained by the conversion of 2-amino-2-deoxy-D-glucose into D-glucose, and the operation, in S. fradiae, of some version of the glucuronate pathway for the removal of C-6 of D-glucose. 

CAS 61-19-8. C10H14N5O7P. The monophosphoric ester of adenosine, i.e., the nucleotide containing adenine, d-ribose, and phosphoric acid. Adenylic acid is a constituent of many important coenzymes. Cyclic adenosine-3, 5 -monophosphate is designated by biochemists as cAMP. 

Fig. 10. SERS spectra of poly-A and its building stones adenine, adenosine 5 -monophosphate and ribose 5-phosphate. Freshly prepared silver colloids, pH 4.5 4 x 10 M adenine, 5 -AMP or ribose 5-phosphate added poly-A concentration 1.6mg/ml Laser excitation line 514nm, laser power 200 mW. (The drawing of poly-A in d shows the adenine base and the sugar-phosphate backbone outside the molecule)...

Nucleotides, nucleoside phosphates phosphoric acid esters of Nucleosides (see). o-Phosphoric add is esterified with a free OH-group of the sugar. If the sugar is D-ribose, the N. is called a ribonucleotide or ribotide. If the sugar is o-2-deoxyribose, the N. is a deoxyribonucleotide, deoxynucleotide or deoxyribo-tide. The phosphate may be present on position 2, 3 or 5 (in deoxyribonucleotides, only the 3 - and 5 -phosphate are possible). 5 -nucleoside phosphates are metabolically very important they may be mono-, di- or triphosphorylated, e.g. guanosine S -monophosphate, cytidine 5 -diphosphate and adenosine 5 -triphosphate. 

Nucleotides are named as the 3 - or 5 -monophosphate esters of a nucleoside, as shown above. These names are frequently abbreviated as in Table 18.1. In these abbreviations, letter d stands for 2-deoxy-D-ribose, the next letter refers to the heterocyclic base, and MP stands for monophosphate. (Later we will see that some nucleotides are diphosphates, abbreviated DP, or triphosphates, TP.) Unless otherwise stated, the abbreviations usually refer to the 5 -phosphates. 

The jS-D-glucosidase of Mucor racemosus was shown to be biosynthesized when the organism was grown in the presence of such diverse carbon sources as glycerol, lactate, o-xylose, o-ribose, methyl and phenyl a-o-glucopyrano-sides, maltose, and cellobiose. Enzyme biosynthesis was strongly repressed in the presence of hexoses and of adenosine 3, 5 -monophosphate. The role of adenosine 3, 5 -monophosphate in the control of jS-D-glucosidase synthesis in M. racemosus was discussed. 

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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