Nicotinamide adenine dinudeotide

Price, R., Gaber, B. and Lvov, Y. (2001) In-vitro release characteristics of tetracycline, khellin and nicotinamide adenine dinudeotide from halloysite a cylindrical mineral for delivery of biologically active agents. Journal of Microencapsulation, 18, 713—723. 

In view of the oxidant nature of ozone, a number of investigators have evaluated its effects on intracellular compounds that are normally active in cellular redox reactions. Attention has focused particularly on reduced pyridine nucleotides—reduced nicotinamide adenine dinudeotide (NADH) and reduced nicotinamide adenine dinucleotide phosphate (NADPH)— and on sulfhydryl compounds, specifically reduced glutathione (GSH). 

Schwer, B., North, B.J., Frye, R.A., Ott, M. and Verdin, E. (2002) The human silent information regulator (Sir)2 homologue hSIRT3 is a mitochondrial nicotinamide adenine dinudeotide-dependent deacetylase. The Journal of Cell Biology, 158, 647-657. 

Nicotinamide adenine dinudeotide phosphate, reduced New chemical entity Oral contraceptive... 

Insects poisoned with rotenone exhibit a steady decline in oxygen consumption and the insecticide has been shown to have a specific action in interfering with the electron transport involved in the oxidation of reduced nicotinamide adenine dinudeotide (NADH) to nicotinamide adenine dinucleotide (NAD) by cytochrome h. Poisoning, therefore, inhibits the mitochondrial oxidation of Krebs-cycle intermediates which is catalyzed by NAD. 

NADP = nicotinamide-adenine dinucleotide phosphate NADPH = reduced nicotinamide—adenine dinudeotide phosphate NDP = nucleoside... 

The biological importance of these compounds stems from their use as cofactors. Both nicotinamide and nicotinic acid are building blocks for coenzyme I (Co I), nicotinarnide—adenine dinucleotide (NAD) (3) and coenzyme 11 (Co II), nicotinamide—adenine dinudeotide phosphate (NADP) (4) (2). 

For these reasons, recent efforts have been aimed at cheap, effident cofactor recycle systems for use with cell-free alcohol dehydrogenase preparations. Regeneration of the nicotinamide adenine dinudeotide cofactor required for alcohol synthesis can be catalyzed by a second enzyme or reduced by the same enzjme, provided the overall equilibrium is favorable. 

Formate dehydrogenase in conjunction with polyethyleneglycol-immobilized nicotinamide adenine dinudeotide has been used to good effect as a cofactor recycle system (39). The alcohol dehydrogenase from Thermoanaerobium hrockii catalyzed the reduction of ketones independently when driven by the cooxidation of isopropanol (40,41). 

Figure 21 -8 Major glycolytic pathways of the erythrocyte. Substrates are in uppercase type, and enzymes are in parentheses. EMP, The Embden-Meyerhof pathway HMP hexose monophosphate pathway or pentose shunt RLC, the Rapoport-Luebering cycle ADP, adenosine diphosphate ATP, adenosine triphosphate NAD, nicotinamide-adenine dinudeotide NADH, reduced nicotinamide-adenine dinucleotide NADP, nicotinamide-adenine dinucleotide phosphate NADPH, reduced nicotinamide-adenine dinucleotide phosphate.The step from ribulose-5-phosphate, which is shown as being catalyzed by transketolase and transaldolase, is an abbreviation of this portion of the HMR...

Nicotinamide adenine dinudeotide (NADH)-cytochrome b5 reductase (EC 1.6.2.2 cytbSr) uses NADH generated in the reaction in the Embden-Meyerhof pathway by glycer-aldehyde 3-phosphate dehydrogenase, to reduce the 12kDa protein cytochrome b5. Cytochrome b5 in turn reduces methemoglobm to hemoglobin. 

Figure 1513 Structures of the oxidized forms of nicotinamide-derived electron carriers. Nicotinamide adenine dinudeotide NAD ) and nicotinamide adenine dinudeotide phosphate (NADP ) are prominent carriers of high-energy electrons. In NAD, R - H in NADP".

Nicotinamide adenine dinudeotide is a major electron carrier in the oxidation of fuel molecules (Figure 15.13). The reactive part of NAD is its nicotinamide ring, a pyridine derivative synthesized from the vitamin niacin. In the oxidation of a substrate, the nicotinamide ring of NAD a hydrogen ion and two electrons, which are equivalent to a hydride ion (H ). The reduced form of this carrier is called NADH, In the oxidized form, the nitrogen atom carries a positive charge, as indicated by NAD. the electron acceptor in many reactions of the type... 

Another nucleoside-derived mechanism-based enzyme inhibitor is Fluoronepla-nocin A [79]. This compound is of interest as a broad-spectrum antiviral drug which acts by irreversible inhibition of S-adenosylhomocystein hydrolase (SAH). In a first enzymatic reaction step the 3 -hydroxy group of the inhibitor is oxidized to the corresponding ketone (Scheme 4.34). This leads to depletion of the biochemical oxidizer nicotinamide adenine dinudeotide (NAD ). In the next step a nucleophilic residue of the enzyme undergoes Michael addition to the /i-fluoro a,/>-unsatu-rated ketone moiety. This is followed by fluoride elimination and thus the inhibitor stays covalently trapped in the active site and disables the enzyme permanently. 

Chen, L., Petrelli, R., Felczak, K., et al. (2008) Nicotinamide adenine dinudeotide based therapeutics. Curr. Med. Chem. 15,650-670. 

Zerez, C. R., Roth, E. F., Jr., Schulman, S., and Tanaka, K. R. (1990). Increased nicotinamide adenine dinudeotide content and synthesis in Plasmodium falciparum-infected human erythrocytes. Blood 75,1705-1710. 

Abbreviations used NAD+ = nicotinamide adenine dinucleotide NADH e reduced nicotinamide adenine dinucleotide NADP = nicotinamide adenine dinudeotide phosphate NAD PH reduced nicotinamide adenine dinucleotide phosphate NMN, NMN+ nicotinamide mononucleotide NMNH2 = reduced nicotinamide mononucleotide a-NAD a-nicotinamide adenine dinucleotide AMP = 5 -adenylic acid 3,5 -AMP adenosine 3, 5 -cycIic phosphate 3 ,5 -UMP = uridine 3, 5 -cyclic phosphate 3, 5 -CMP cytidine 3, 5-cyclic phosphate 3 f5 GMP = guanosine 3 5f-cyclic phosphate 3, 5 TMP thymidine 3, 5 -cyclic phosphate Dibutyryl-3, 5 -AMP = N6,02-dibutyryladenosine 3, 5 -cyclic phosphate 2, 3 -UMP = uridine 2 ,3 -cyclic monophosphate 2, 3 -CMP cytidine 2, 3 -cyclic monophosphate 2, 3 -AMP = adenosine 2, 3 -cyclic monophosphate 2 ,3 -GMP = guanosine 2 3 -cyclic monophosphate 2 -UMP = uridine 2 -phosphate -UMP uridine -phosphate 5 -UMP = uridine 5 phosphate Poly U polyuridylic acid ADP = adenosine 5 -diphosphate FAD = flavin adenine dinucleotide UpA, UpU, ApU and ApA x dinucleoside phosphates of uridine and/or adenine. c See original references for experimental conditions and additional data. 

Figure 8.2 Malate Dehydrogenase (MDH). (a) Reversible reaction catalyzed by MDH where NADH is nicotinamide adenine dinucleotide, reduced form (b) ribbon display structure of MDH (porcine heart) (side view) (pdb 4mdh). The homo-dimeric protein consists of two polypeptides chains (yellow and red), with nicotinamide adenine dinudeotide (NAD+) in both independent catalytic sites illustrated in a ball and stick (blue) representation (c) chemical illustration of the tricarboxylic acid cycle (TCA) to demonstrate the importance of MDH catalysis in cycle closure. Enzyme abbreviations are PDH, pyruvate dehyrogensase CS, citrate synthase.

The key step for alcohol oxidation by nature s reagent, nicotinamide adenine dinudeotide (NAD" ), is given in the mechanism above. Use that reaction for the reduction of NAD" to answer the following questions. 

Amar-Costesec, A., Prado Figueroa, M., Beaufay, H., Nagelkerke, J.F., van Berkel, T.J.C., 1985. Analytical study of rnicrosomes and isolated suboeUular mernbranes from rat liver. IX. Nicotinamide adenine dinudeotide glycohydrolase a plasma membrane enzyme prominently found in Kupffer cells. Journal of Cell Biology 100,189-197. 

NAD(P)H nicotinamide adenine dinudeotide (phosphate), reduced form... 

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