Adenine protonation

Nielsen SB, Soiling TI (2005) Are conical intersections responsible for the ultrafast processes of adenine, protonated adenine, and the corresponding nucleosides . Chem Phys Chem 6 1276... 

Responsible for the Ultrafast Processes of Adenine, Protonated Adenine, and the Corresponding Nucleosides ... 

Adenine is a weak base Which one of the three nitrogens designated by arrows in the struc tural formula shown is protonated in acidic solution" A resonance evaluation of the three protonated forms will tell you which one is the most stable... 

Fig. 2. Homeostatic control of blood Ca " level where PTH is parathyroid hormone [9002-64-6], CC, cholecalciferol, ie, vitamin D HCC, hydroxycholecalciferol DHCC, dihydroxycholecalciferol CaBP, calcium-binding protein NAD PH, protonated nicotinarnide-adenine dinucleotide...

Adenine, 9-a,/3-D-glucopyranosyl-synthesis, 5, 594 Adenine, N -isopentenyl-occurrence, 5, 601 Adenine, 1-methyl-methylation, S, 530 synthesis, 5, 594 Adenine, 2-methyl-synthesis, 5, 570, 572 Adenine, 3-methyl-methylation, 5, 530 synthesis, 5, 586, 595 Adenine, 7-methyl-methylation, 5, 530 protonation, 5, 509 synthesis, 5, 585... 

The examples in the fourth column (Table IX) concern the protonation of purine and adenine and their derivatives while those of the last column mainly reflect Kleinpeter s contributions (Table VIII) to the functional tau-tomerism of 7-hydroxy-l,2,4-triazolo[l,5-a]pyrimidines. 

Complex V 370 kDa About 16 3 bound adenine nucleotides Base (FJ spans membrane, connected to F, on inner face 0.52-0.54 Translocates protons across membrane, is associated with ATP synthesis, or with ATP hydrolysis... 

Complex II contains four peptides, the two largest form succinate dehydrogenase, the largest has covalently boiuid flavin adenine dinucleotide (FAD) which reacts with succinate, and the other has three iron-sulphur centers. Smaller subunits anchor the two larger subunits to the membrane and form the UQ binding site. Ubiquinone is the electron acceptor but complex II does not pump protons (see below). 

Figure 12-11. Combination of phosphate transporter ( ) with the adenine nucleotide transporter ((2)) in ATP synthesis. The H+ZP, symport shown is equivalent to the P /OH antiport shown in Figure 12-10. Four protons are taken into the mitochondrion for each ATP exported. However, one less proton would be taken in when ATP is used inside the mitochondrion.

Zinc-containing alcohol dehydrogenases take up two electrons and a proton from alcohols in the form of a hydride. The hydride acceptor is usually NAD(P) (the oxidized form of nicotinamide adenine dinucleotide (NADH) or its phosphorylated derivative, NADPH). Several liver alcohol dehydrogenases have been structurally characterized, and Pig. 17.8 shows the environment around the catalytic Zn center and the bound NADH cofactor. 

Figure 18.2 Summary of respiratory energy flows. Foods ate converted into the reduced form of nicotinamide adenine dinucleotide (NADH), a strong reductant, which is the most reducing of the respiratory electron carriers (donors). Respiration can he based on a variety of terminal oxidants, such as O2, nitrate, or fumarate. Of those, O2 is the strongest, so that aerobic respiration extracts the largest amount of free energy from a given amount of food. In aerobic respiration, NADH is not oxidized directly by O2 rather, the reaction proceeds through intermediate electron carriers, such as the quinone/quinol couple and cytochrome c. The most efficient respiratory pathway is based on oxidation of ferrocytochrome c (Fe ) with O2 catalyzed by cytochrome c oxidase (CcO). Of the 550 mV difference between the standard potentials of c)Tochrome c and O2, CcO converts 450 mV into proton-motive force (see the text for further details).

The oxidation of reduced jS-nicotinamide adenine dinucleotide (NADH) by quinone derivatives (Q) by has been investigated extensively, since the reaction was considered to be essential in the proton transport and the energy accumulation occurring at the mitochondrial inner membrane [2]. However, most of fundamental work in this field has been done in homogeneous solutions [48-52] though the reaction in living bodies has been believed to proceed at the solution membrane interface. 

N3-coordinated complexes containing platinum group metal ions have also been synthesized and studied (56,60,61). Steric hindrance has been used to direct binding to N3 in a series of Pd- and Pt-containing complexes of 6,6,9-trimethyladenine (60). Platinum modification was found to have a pronounced effect on the basicity of the adenine moiety. The protonation constants (log Kh values) for the twofold protonation of 6,6,9-trimethyladenine are 4.15 and -0.75, with the initial protonation occurring at N1 followed by N7. The equivalent values for the formation of [Pt(dien)TMA-A3)H]3+ and [Pt(dien)TMA-2V3)H2]4+ are 0.3 and —1.2, respectively. Moreover, the site of initial protonation was found to be N7 (Fig. 19). These observations are supported by theoretical studies (62). 

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