NADP p-Nicotinamide adenine dinucleotide phosphate

NADP, p-nicotinamide adenine dinucleotide phosphate NADPH, reduced NADP... 

NAD P-nicotinamide-adenine dinucleotide, reduced form NADP P-nicotinamide-adenine dinucleotide phosphate, oxidized form... 

P-Nicotinamide adenine dinucleotide phosphate (NADP, TPN) [53-59-8] M 743.4, pKi 1.1 (PO4H2), pK2 4.0 (adenine NH2), PK3 6.1 (P04 ). Purified by anion-exchange chromatography in much the same way as for NAD [Dalziel and Dickinson Biochem 7 95 311 1965 Biochemical Preparations 11 87 1966]. Finally it is purified by dissolving in H2O and precipitating with 4 volumes of Me2CO and dried in... 

P-Nicotinamide adenine dinucleotide phosphate reduced tetrasodium salt (reduced diphosphopyridine nucleotide phosphate sodium salt, NADPH) [2646-71-1] M 833.4, pK as for NADP. Mostly similar to NADH above. 

Nicotinamide is an essential part of two important coenzymes nicotinamide adenine dinucleotide (NAD ) and nicotinamide adenine dinucleotide phosphate (NADP ) (Figure 18.19). The reduced forms of these coenzymes are NADH and NADPH. The nieotinamide eoenzymes (also known as pyridine nucleotides) are electron carriers. They play vital roles in a variety of enzyme-catalyzed oxidation-reduction reactions. (NAD is an electron acceptor in oxidative (catabolic) pathways and NADPH is an electron donor in reductive (biosynthetic) pathways.) These reactions involve direct transfer of hydride anion either to NAD(P) or from NAD(P)H. The enzymes that facilitate such... 

Two derivatives of nicotinamide (pyridine-3-carboxylic amide), one of the B2 vitamins, nicotinamide adenine dinucleotide (NAD ) and nicotinamide adenine dinucleotide phosphate (NADP ), serve as redox coenzymes. Of the three heterocyclic ring systems found in these coenzymes, i.e. those of purine, ribose and pyridine, it is the pyridine portion that is reactive in redox reactions. Biologically, two oxidation states are important the oxidized form, NAD(P)+, and the 1,4-dihydro isomer of the two-electron reduced form, NAD(P)H (Scheme 1). Nicotinamide coenzymes interconvert between these two oxidation states in... 

FIGURE 1.12 A simplified scheme for the mechanism of action of cytochrome P-450. NADP = nicotinamide-adenine dinucleotide phosphate, NADPH = the reduced form of NADP. 

Nicotinamide is the reactive moiety of the nicotinamide nucleotide coenzymes NAD (nicotinamide adenine dinucleotide) and NADP (nicotinamide adenine dinucleotide phosphate), which are coenzymes (or more correctly cosubstrates) in a wide variety of oxidation and reduction reactions (Section 8.4.1). The notation NAD(P) is used to mean either NAD or NADP, without specifying the oxidation state. 

Figure 5.4 Outline of the newly discovered glyceraldehyde phosphate/pyruvate pathway for the formation of C5 isoprenoid units. None of the intermediates after 2-C-methyl-D-erythritol 4-phosphate is known. P indicates a phosphate moiety. TPP, thiamine pyrophosphate NADP, nicotinamide adenine dinucleotide phosphate.

Fig. 2.1. Examples from The Energy Hall of Fame. These molecules not only deliver energy, but transfer special groups in the process. Acyl, RCO— ADP, adenosine diphosphate ATP, adenosine triphosphate dUMP deoxyuridine monophosphate FAD, flavin adenine dinucleotide GTP, guanosine triphosphate NADH, nicotinamide adenine dinucleotide NADP, nicotinamide adenine dinucleotide phosphate P, phosphate TMP, thymidine monophosphate UDP, uridine diphosphate UTP, uridine triphosphate.

Nicotinamide adenine dinucleotide (NAD and its reduced form dihydronicotinamide adenine dinucleotide (NADH)) as well as nicotinamide adenine dinucleotide phosphate (NADP and its reduced form nicotinamide adenine dinucleotide phosphate hydrogen (NADPH)) are essential co-factors for many dehydrogenases. The presence of NAD was first demonstrated in P. gallinaceum (Speck and Evans, 1945) and later studies showed increased levels of these pyridine nucleotides in P. lophurae, P. berghei and P. falciparum. Trager (1977) reported that high levels of... 

Fig. 11 Biochemical pathways for the formation, detoxification, and cellular effects of xenobiotic free radical intermediates and reactive oxygen species (ROS). Fe iron, G-6-P glucose-6-phos-phate, GSH glutathione, GSSG glutathione disulfide, H2O2 hydrogen peroxide, FIO hydroxyl radical, LPO lipoxygenase, NADP nicotinamide adenine dinucleotide phosphate, O2 superoxide, P450 cytochromes P450, PHS prostaglandin H synthase, SOD superoxide dismutase. (Modified from Wells et al. 1997)...

Electrochemical transformations of nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) have been dealt with in several publications, since they are the most important hydrogen carriers. There are reviews on this topic/" The standard redox potential of the NAD(P)H/NAD(P) couple has been found to be —0.32... 

Superoxide production from paraquat in a pig pulmonary microvascular endotheUal cell suspension was demonstrated by Tampo et al. (1999) using 2-methyl-6-(p-methoxyphenyl)-3,7-dihydroimidazol[l,2-a]pyrazin-3-one, a chemiluminescence probe, to detect superoxide anions. Increased rates of superoxide production from paraquat, which were sensitive to superoxide dismutase, required the presence of reduced nicotinamide adenine dinucleotide phosphate (NADPH) in the reaction medium, and occurred instantaneously after the addition of NADPH, which is impermeable to cell membranes. NADH as an electron donor was not as effective, and xanthine or succinate had no influence. Paraquat was anaerobically reduced in the presence of NADPH and 2-methyl-6-(p-metho-xyphenyl) - 3,7 - dihydroimidazol[l,2 - ajpyrazin- 3 -one to yield a one-electron reduced radical, and the reduction was inhibited by NADP". Diphenyleneio-donium, an inhibitor of flavoprotein reductase, also markedly inhibited both paraquat reduction and superoxide production. 

Abbreviations used are PP-ribose-P, a-5-phosphoribosyl-1-pyrophosphate PRA, 3-5-phosphoribosyl-l-amine GAR, glycinamide-ribonucleotide formyl-GAR, a-formyl-GAR formyl-GAM, a-formyl gly-cinamidineribonucleotide IMP, inosine 5 -monophosphate AMP, adenosine 5 -monophosphate GMP, guanosine 5 -monophosphate PPi, inorganic pyrophosphate CoA-SH, reduced coenzyme A NADP, nicotinamide adenine dinucleotide phosphate PRT, hypoxanthine-guanine phosphoribosyltransferase. 

EC 2.7.1.33) to N-(i )-4 -phosphopantothenate. Activation of the carboxylate results from the addition of P-alanine (P-alanine is formed on decarboxylation of aspartate [Asp, D], EC 4.1.1.11), by cytidylate formation (cytosine triphosphate [CTP] is followed by coupling to L-cysteine (Cys, C) (EC 6.3.2.S) to produce N-[(i )-4 -phosphopantothienoyl]-L-< steine. Oxidation to the thioaldehyde with flavin mononucleotide (EMN FMNH2) allows decarboxylation of the latter with the formation of the corresponding enol. Then, reduction with nicotinamide adenine dinucleotide phosphate (NADPH/IT NADP) (EC 4.1.1.36) leads to 4-phosphopantetheine (pantetheine 4 -phosphate). 

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