58-68-4 (二氢烟酰胺-腺嘌呤二核苷酸,Adenosine 5'-(trihydrogen diphosphate), P'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide)

快速询单

结构式：

二氢烟酰胺-腺嘌呤二核苷酸MOL文件

CAS号：

58-68-4

中文名称：

二氢烟酰胺-腺嘌呤二核苷酸

英文名称：

Adenosine 5'-(trihydrogen diphosphate), P'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide

分子式：

C₂₁H₂₉N₇O₁₄P₂

分子量：

665.440986394882

植物源：

拟南芥

二氢烟酰胺-腺嘌呤二核苷酸(58-68-4)名称与标识符

名称

中文别名：

二氢烟酰胺-腺嘌呤二核苷酸;

英文别名：

Adenosine5'-(trihydrogen diphosphate), P'®dihydronicotinamide-adenine dinucleotide;Reduced nicotinamide-adenine dinucleotide;5'-ester with 1,4-dihydro-1-b-D-ribofuranosyl-3-pyridinecarboxamide; β- NADH; β-DPNH; Reduced nicotinamide-adenine dinucleotide (NADH); Reduced nicotinamide-adenine dinucleotide; Reduced nicotinamide adenine diphosphate; Reduced diphosphopyridine nucleotide; Reduced codehydrogenase I; Nicotinamide-adenine dinucleotide, reduced; Nicotinamide adenine dinucleotide 2 (reduced form); NADH ; N 8129; ENADA; Dihydronicotinamide mononucleotide; Dihydronicotinamide adenine dinucleotide; Dihydrocozymase; Dihydrocodehydrogenase I; DPNH; Cozymase I, reduced; Coenzyme I, reduced; Codehydrogenase I, reduced; Codehydrase I, reduced; 1,4-Dihydronicotinamide adenine dinucleotide; Adenosine pyrophosphate, 5'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosylnicotinamide (7CI);Adenosine 5'-(trihydrogen pyrophosphate), 5'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosylnicotinamide (8CI);Adenosine 5'-(trihydrogen diphosphate), P'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide;Coenzyme I, reduced;NAD-reduced;dihydrodiphosphopyridine nucleotide;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate;nadh hydride;Codehydrogenase I, reduced;bmse000054;C00004;NADH;Adenosine pyrophosphate, 5'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosylnicotinamide (7CI);CHEBI:16908;Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosylnicotinamide (8CI);D0B8SV;Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide, disodium salt;SCHEMBL8187;CHEMBL1234616;nicotinamide adenine dinucleotide (reduced);NADH [WHO-DD];Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide;4J24DQ0916;dihydronicotinamide adenine dinucleotide;Adenosine 5'-(trihydrogen diphosphate), 5'->'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide;DB00157;Dihydrocozymase;Adenosine 5'-(trihydrogen diphosphate), 5'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide, disodium salt;1,4-Dihydronicotinamide adenine dinucleotide;Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide;DPNH;UNII-4J24DQ0916;606-68-8;Adenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide;NADH2;Nicotinaminde-Adenine-Dinucleotide;Q26987453;Reduced Nicotinamide Adenine Dinucleotide;beta-NADH;[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate;diphosphopyridine nucleotide reduced;C21H29N7O14P2;Nicotinamide adenine dinucleotide, reduced form;ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'->5'-ESTER WITH 1,4-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-3-PYRIDINECARBOXAMIDE;Adenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide (9CI);b-NADH;Dihydronicotinamide mononucleotide;Nicotinamide-adenine dinucleotide, reduced;C21-H29-N7-O14-P2.2Na;C21-H29-N7-O14-P2;[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-phosphinic acid;EINECS 200-393-0;b-dpnh;coenzyme-I;adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] diphosphate}; cent-dpnh;Codehydrase I, reduced;Reduced codehydrogenase I;Nicotinamide - adenine dinucleotide, reduced;beta-DPNH;BOPGDPNILDQYTO-NNYOXOHSSA-N;Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 1,4-dihydro-1beta-D-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate), P'-->5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide;EN300-19742425;[5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [[5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate;58-68-4;NADH+H+;NAD REDUCED FORM [MI];[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid;Dihydrocodehydrogenase I;Cozymase I, reduced;DTXSID30889320;GTPL4487;NAD reduced form;Adenosine 5'-(trihydrogen diphosphate), 5'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide;ENADA;Diphosphopyridine nucleotide,reduced form;Reduced diphosphopyridine nucleotide;C21H29N7O14P2.2Na;Reduced nicotinamide adenine diphosphate;Adenosine 5'-(trihydrogen diphosphate), P'?5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide, disodium salt;adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate};Adenosine pyrophosphate, 5'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosylnicotinamide (7CI);N 8129;Nicotinamide adenine dinucleotide (reduced form);Reduced nicotinamide-adenine dinucleotide (NADH);β-DPNH;β-NADH;((2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl)methoxy-((((2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl)methoxy)hydroxyphosphoryl)oxyphosphinic acid;NADH dianion;BRD-A84188517-304-01-1;Adenosine 5'-(trihydrogen diphosphate), P'a5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide;HY-113355;CS-0062281;

标识符

MDL：

MFCD00171241

InChIKey：

BOPGDPNILDQYTO-NNYOXOHSSA-N

Inchi：

1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

SMILES：

P(=O)(O)(OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=CCC(C(N)=O)=C2)O1)O)O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3C(N)=NC=NC2=3)O1)O)O

二氢烟酰胺-腺嘌呤二核苷酸(58-68-4)物化性质

计算特性

精确分子量 : 665.12477262g/mol
氢键供体数量 : 8
氢键受体数量 : 19
可旋转化学键数量 : 11
同位素质量 : 665.12477262g/mol
重原子数量 : 44
复杂度 : 1230
同位素原子数量 : 0
确定原子立构中心数量 : 8
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : -5.7
拓扑分子极性表面积 : 318Å²

二氢烟酰胺-腺嘌呤二核苷酸(58-68-4)推荐厂家更多厂家(8)

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二氢烟酰胺-腺嘌呤二核苷酸(58-68-4)合成路线

合成路线：1 步

反应条件：

1.1R:H2, C:Pt, S:H2O, 2 h, 37°C, 10 atm, pH 10

参考文献：

NADH Regeneration: A Case Study of Pt-Catalyzed NAD+ Reduction with H2

By Saba, Tony et al, ACS Catalysis, 2021, 11(1), 283-289

合成路线：1 步

反应条件：

1.1R:HCO2- •Na+, C:254734-81-1, C:6234-26-0, S:H2O, 40°C, pH 6.25

参考文献：

Iridium(2+), triaqua[(1,2,3,4,5-)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]-, sulfate (1:1)

By Noshi, Mohammad N., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2014, From e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-4

合成路线：1 步

反应条件：

1.1S:H2O, 16 h, 50°C

参考文献：

Factors influencing the operational stability of NADPH-dependent alcohol dehydrogenase and an NADH-dependent variant thereof in gas/solid reactors

By Kulishova, Liliya et al, Journal of Molecular Catalysis B: Enzymatic, 2010, 67(3-4), 271-283

合成路线：1 步

反应条件：

1.1R:HCO2- •Na+, R:(NH4)2SO4, C:1449222-31-4, S:H2O, 1.5 h, < 40°C, pH 7.4; 1 h, < 40°C, pH 7.4
1.2R:PhNCS, R:Et3N, S:MeCN, 1 h, rt

参考文献：

The visible-light-driven transfer hydrogenation of nicotinamide cofactors with a robust ruthenium complex photocatalyst

By Dong, Wenjin et al, Green Chemistry, 2020, 22(7), 2279-2287

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:R:(L)-Ascorbic acid, C:22843-73-8, C:143334-20-7

参考文献：

Solar Light Responsive Graphitic Carbon Nitride Coupled Porphyrin Photocatalyst that Uses for Solar Fine Chemical Production

By Mishra, Shaifali et al, Photochemistry and Photobiology, 2023, 99(4), 1080-1091

合成路线：1 步

53-84-9

_65%

58-68-4

反应条件：

1.1R:C:15086-94-9 (reaction products with aminomethylpolystyr), C:2920852-50-0, S:H2O

参考文献：

Polystyrene-based eosin-Y as a photocatalyst for solar light-mediated NADH/NADPH regeneration and organic transformations

By Singh, Pooja et al, Reaction Chemistry & Engineering, 2023, 8(5), 1072-1082

合成路线：1 步

反应条件：

1.1S:H2O, pH 7

参考文献：

Enzymatic electrosynthesis of glycine from CO2 and NH3

By Wu, Ranran et al, Angewandte Chemie, 2023, 62(14), e202218387

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:HCl, S:H2O, 2 h, rt

参考文献：

Modular engineering strategy to redirect electron flux into the electron-transfer chain for enhancing extracellular electron transfer in Shewanella oneidensis

By Ding, Qinran et al, ACS Synthetic Biology, 2023, 12(2), 471-481

合成路线：1 步

反应条件：

1.1R:O2, C:9028-14-2, S:H2O, pH 9.5

参考文献：

Aerobic photobiocatalysis enabled by combining core-shell nanophotoreactors and native enzymes

By Wei, Wenxin et al, Journal of the American Chemical Society, 2022, 144(16), 7320-7326

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1C:108120-95-2, S:H2O, 10 min, pH 7.4

参考文献：

Non-covalent metalation of carbon nitride for photocatalytic NADH regeneration and enzymatic CO2 reduction

By Zhang, Yuanyuan et al, Chemical Communications (Cambridge, 2022, 58(78), 10997-11000

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:N(CH2CH2OH)3, C:42712-11-8, C:Rh, C:9003-39-8, C:TiO2, S:H2O, 30°C, pH 7.4

参考文献：

Visible-light-induced enzymatic reactions using an NADH regeneration system of water-soluble zinc porphyrin and homogeneous colloidal rhodium nanoparticles

By Katagiri, Takayuki and Amao, Yutaka, Sustainable Energy & Fuels, 2022, 6(10), 2581-2592

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:R:N(CH2CH2OH)3, C:Rh (PVP complexes), C:9003-39-8 (rhodium complexes), C:9001-60-9, S:H2O, 30°C, pH 7.4

参考文献：

Visible light driven selective NADH regeneration using a system of water-soluble zinc porphyrin and homogeneous polymer-dispersed rhodium nanoparticles

By Katagiri, Takayuki and Amao, Yutaka, New Journal of Chemistry, 2021, 45(35), 15748-15752

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1

参考文献：

Accelerated green process of 2,5-dimethylpyrazine prodn. from glucose by genetically modified Escherichia coli

By Xu, Jianzhong et al, ACS Synthetic Biology, 2020, 9(9), 2576-2587

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:Et3N, R:NaH2PO4, C:2738613-29-9, S:MeCN, S:H2O, 50°C

参考文献：

Pyrimidoquinxoalinophenanthroline opens next chapter in design of bridging ligands for artificial photosynthesis

By Brueckmann, Jannik et al, ChemRxiv, 2021, From ChemRxiv, 1-19

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:H2, C:Pt, S:H2O, 37°C, 1 atm, pH 8.7

参考文献：

Chemoselective NADH Regeneration: the Synergy Effect of TiOx and Pt in NAD+ Hydrogenation

By Wang, Maodi et al, ACS Sustainable Chemistry & Engineering, 2021, 9(18), 6499-6506

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:HCO2- •Na+, C:60168-55-0 (solid solns. with EtOH analog), S:H2O, S:EtOH

参考文献：

Can a Nonorganometallic Ruthenium(II) Polypyridylamine Complex Catalyze Hydride Transfer? Mechanistic Insight from Solution Kinetics on the Reduction of Coenzyme NAD+ by Formate

By Chrzanowska, Marta et al, Inorganic Chemistry, 2020, 59(20), 14944-14953

合成路线：1 步

53-84-9

_74%

58-68-4

反应条件：

1.1R:N(CH2CH2OH)3, C:143334-20-7 (thiophene-modified), C:160261-98-3, S:H2O, 30 min, rt, pH 7
1.215 min

参考文献：

A thiophene-modified doubleshell hollow g-C3N4 nanosphere boosts NADH regeneration via synergistic enhancement of charge excitation and separation

By Meng, Jialin et al, Catalysis Science & Technology, 2019, 9(8), 1911-1921

合成路线：1 步

53-84-9

_74%

58-68-4

反应条件：

1.1R:N(CH2CH2OH)3, R:R:HCl, C:2451517-73-8 (imine-cyclized), S:H2O, 30 min, rt, pH 7; 10 min, rt

参考文献：

Construction of fully conjugated covalent organic frameworks via facile linkage conversion for efficient photoenzymatic catalysis

By Wang, Yuancheng et al, Journal of the American Chemical Society, 2020, 142(13), 5958-5963

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:HCO2- •Na+, C:208988-63-0, S:H2O, S:DMSO, 37°C

参考文献：

Fluorescent and Biocompatible Ruthenium-Coordinated Oligo(p-phenylenevinylene) Nanocatalysts for Transfer Hydrogenation in the Mitochondria of Living Cells

By Dai, Nan et al, Chemistry - A European Journal, 2020, 26(20), 4489-4495

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:N(CH2CH2OH)3, R:C:TiO2, C:143334-20-7, S:H2O, 10 min, rt

参考文献：

Coordination between Electron Transfer and Molecule Diffusion through a Bioinspired Amorphous Titania Nanoshell for Photocatalytic Nicotinamide Cofactor Regeneration

By Yang, Dong et al, ACS Catalysis, 2019, 9(12), 11492-11501

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:H2, C:Pt, C:1317-61-9, S:H2O, 25°C, 10 atm, pH 7

参考文献：

Assessing the environmental performance of NADH regeneration methods: A cleaner process using recyclable Pt/Fe3O4 and hydrogen

By Saba, Tony et al, Catalysis Today, 2020, 339, 281-288

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1R:HCO2- •Na+, C:2375190-55-7, 6 h, 37°C, pH 7.4

参考文献：

N,O-Chelating quinoline-based half-sandwich organorhodium and -iridium complexes: synthesis, antiplasmodial activity and preliminary evaluation as transfer hydrogenation catalysts for the reduction of NAD+

By Stringer, Tameryn et al, Dalton Transactions, 2019, 48(35), 13143-13148

合成路线：1 步

1094-61-7

56-65-5

58-68-4

反应条件：

1.1R:MgCl2, R:NaCl, R:KCl, C:9024-82-2, S:H2O, S:EtOH, 30 min, 36.9-37.1°C
1.2C:9032-70-6, 1800 s, 36.9-37.1°C
1.3C:Alcohol dehydrogenase, 300 s, 36.9-37.1°C

参考文献：

Emissive Synthetic Cofactors: A Highly Responsive NAD+ Analogue Reveals Biomolecular Recognition Features

By Feldmann, Jonas et al, Chemistry - A European Journal, 2019, 25(17), 4379-4389

合成路线：1 步

53-84-9

_46%

58-68-4

反应条件：

1.1R:N(CH2CH2OH)3, R:HCl, C:2353523-07-4, C:200212-13-1, S:H2O, rt, pH 8

参考文献：

Fully conjugated two-dimensional sp2-carbon covalent organic frameworks as artificial photosystem I with high efficiency

By Zhao, Yingjie et al, Angewandte Chemie, 2019, 58(16), 5376-5381

合成路线：1 步

反应条件：

1.1R:N(CH2CH2OH)3, C:Carbon (N-doped), C:9001-68-7, C:160261-98-3, S:H2O, 15 min, 45°C, pH 7.5

参考文献：

Biocatalytic C=C Bond Reduction through Carbon Nanodot-Sensitized Regeneration of NADH Analogues

By Kim, Jinhyun et al, Angewandte Chemie, 2018, 57(42), 13825-13828

合成路线：1 步

53-84-9

58-68-4

反应条件：

1.1C:2241650-40-6, S:H2O, 1 h, pH 7

参考文献：

Porphyrin/SiO2/Cp*Rh(bpy)Cl Hybrid Nanoparticles Mimicking Chloroplast with Enhanced Electronic Energy Transfer for Biocatalyzed Artificial Photosynthesis

By Ji, Xiaoyuan et al, Advanced Functional Materials, 2018, 28(9), n/a

合成路线：1 步

53-57-6

58-68-4