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Merck
CN

A5251

3-乙酰吡啶腺嘌呤二核苷酸

≥85%

别名:

3-乙酰基 NAD, APADH, APAD

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关于此项目

经验公式（希尔记法）:
C22H28N6O14P2
化学文摘社编号:
86-08-8
分子量:
662.44
NACRES:
NA.51
PubChem Substance ID:
24890959
UNSPSC Code:
41106305
MDL number:
MFCD00078882

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产品名称

3-乙酰吡啶腺嘌呤二核苷酸, ≥85%

InChI

1S/C22H28N6O14P2/c1-10(29)11-3-2-4-27(5-11)21-17(32)15(30)12(40-21)6-38-43(34,35)42-44(36,37)39-7-13-16(31)18(33)22(41-13)28-9-26-14-19(23)24-8-25-20(14)28/h2-5,8-9,12-13,15-18,21-22,30-33H,6-7H2,1H3,(H3-,23,24,25,34,35,36,37)/t12-,13-,15-,16-,17-,18-,21-,22-/m1/s1

SMILES string

CC(=O)c1ccc[n+](c1)[C@@H]2O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O

InChI key

KPVQNXLUPNWQHM-RBEMOOQDSA-N

biological source

Porcine brain

assay

≥85%

form

powder

Quality Level

200

mol wt

662.44 g/mol

concentration

≤100% (3-acetylpyridine-adenine dinucleotide)

color

white to off-white

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

λmax

259-260 nm

fluorescence

λem 15.2- 17.2 (dry basis at pH 7.0)

storage temp.

−20°C

相关类别

Application

许多分子使用3-乙酰吡啶腺嘌呤二核苷酸作为信号分子、辅因子或底物。各种脱氢酶过程使用APAD代替NAD作为氢接受辅因子。 氧化磷酸化可以用ADAP进行研究。 ADAP也可以用作合适的底物。

Biochem/physiol Actions

APAD是一种NAD类似物，具有比NAD高的氧化电位。在许多脱氢酶反应中可代替 NAD 作为受氢辅助因子；例如， 弓形虫、华支睾吸虫、 和 疟原虫 中的乳酸脱氢酶、细菌硫辛酰胺脱氢酶以及哺乳动物脱氢酶。在与 NADH 或 NADPH 的各种转氢反应中也可作为质子受体。

General description

3-乙酰吡啶腺嘌呤二核苷酸是一种结晶固体。3-乙酰吡啶腺嘌呤二核苷酸在各种交替氧化的酶活动中是一种突出的电子转运体。 APAD比NAD具有更显著的氧化电势。 NAD类似物APAD在电化学上比真正的NAD更有效地还原，其还原产物的稳定性也显著高于NADH。 在与NADH或NADPH的转氢化过程中，APAD也作为质子受体起作用。

Other Notes

NAD 类似物

flash_point_f

Not applicable

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_c

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000486760
0000486759
0000486760
0000486759
0000434681

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T Bizouarn et al.
Biochimica et biophysica acta, 1322(1), 19-32 (1997-12-16)
Transhydrogenase couples the translocation of protons across a membrane to the transfer of reducing equivalents between NAD(H) and NADP(H). Using transhydrogenase from Rhodospirillum rubrum we have examined the pH dependences of the 'forward' and 'reverse' reactions, and of the 'cyclic'
Thomas V Riera et al.
Biochemistry, 47(33), 8689-8696 (2008-07-23)
IMP dehydrogenase (IMPDH) catalyzes two very different chemical transformations, a dehydrogenase reaction and a hydrolysis reaction. The enzyme toggles between the open conformation required for the dehydrogenase reaction and the closed conformation of the hydrolase reaction by moving a mobile
T Bizouarn et al.
Biochimica et biophysica acta, 1320(3), 265-274 (1997-07-04)
Transhydrogenase from mitochondrial and bacterial membranes couples proton translocation to hydride transfer between NAD(H) and NADP(H). The enzyme has three domains, of which domains I and III protrude from the membrane. These possess the NAD(H)- and NADP(H)-binding sites, respectively, whereas
S N Stilwell et al.
Biochimica et biophysica acta, 1320(1), 83-94 (1997-05-16)
Transhydrogenase is a proton pump. It has separate binding sites for NAD+/NADH (on domain I of the protein) and for NADP+/NADPH (on domain III). Purified, detergent-dispersed transhydrogenase from Escherichia coli catalyses the reduction of the NAD+ analogue, acetylpyridine adenine dinucleotide
P D Bragg
FEBS letters, 397(1), 93-96 (1996-11-11)
The pyridine nucleotide transhydrogenase is a proton pump which catalyzes the reversible transfer of a hydride ion equivalent between NAD+ and NADP+ coupled to translocation of protons across the cytoplasmic membrane. The enzyme also catalyzes the reduction of the NAD+
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