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A5251

Sigma-Aldrich

3-Acetylpyridine adenine dinucleotide

≥85%

Synonyme(s) :

3 -Acetyl NAD, APADH, APAD

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About This Item

Formule empirique (notation de Hill):
C22H28N6O14P2
Numéro CAS:
86-08-8
Poids moléculaire :
662.44
Numéro MDL:
MFCD00078882
Code UNSPSC :
41106305
ID de substance PubChem :
24890959
Nomenclature NACRES :
NA.51

Source biologique

Porcine brain

Niveau de qualité

200

Pureté

≥85%

Forme

powder

Solubilité

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

Température de stockage

−20°C

Chaîne SMILES 

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

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

Clé InChI

KPVQNXLUPNWQHM-RBEMOOQDSA-N

Description générale

3-Acetylpyridine adenine dinucleotide is a crystalline solid. 3-Acetylpyridine adenine dinucleotide is a prominent electron transporter in various enzymatic activities in which it is alternately oxidized. APAD has a more significant oxidation potential than NAD. NAD analogues, APAD, were electrochemically more effectively reduced than genuine NAD, and the stability of their reduced products was also significantly higher than NADH. In transhydrogenation processes with NADH or NADPH, APAD also operates as a proton acceptor.

Application

Many molecules use 3-Acetylpyridine adenine dinucleotide as a signaling molecule, cofactor, or substrate. Various dehydrogenase processes use APAD instead of NAD as a hydrogen-accepting cofactor. The oxidative phosphorylation can be studied with ADAP. ADAP can also be used as a suitable substrate.

Actions biochimiques/physiologiques

APAD is an NAD analog with higher oxidation potential than NAD. It can substitute for NAD as a hydrogen-accepting cofactor in many dehydrogenase reactions; e.g. lactate dehydrogenase from Toxoplasma, Clonorchis, and Plasmodium, bacterial lipoamide dehydrogenase, as well as mammalian dehydrogenases. It can also act as a proton acceptor in various transhydrogenation reactions with NADH or NADPH.

Liaison

Analog of NAD

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

P D Bragg et al.
Archives of biochemistry and biophysics, 363(1), 182-190 (1999-03-02)
The pyridine nucleotide transhydrogenase carries out transmembrane proton translocation coupled to transfer of a hydride ion equivalent between NAD+ and NADP+. Previous workers (E. Holmberg et al. Biochemistry 33, 7691-7700, 1994; N. A. Glavas et al. Biochemistry 34, 7694-7702, 1995)
M Yamaguchi et al.
Biochimica et biophysica acta, 1318(1-2), 225-234 (1997-01-16)
The hydrophilic, extramembranous domains I (alpha 1 subunit) and III of the Rhodospirillum rubrum nicotinamide nucleotide transhydrogenase were expressed in Escherichia coli and purified therefrom as soluble proteins. These domains bind NAD(H) and NADP(H). respectively, and together they form the
Todd W Roy et al.
Nucleic acids research, 35(21), e147-e147 (2007-11-16)
The Escherichia coli AlkB protein catalyzes the direct reversal of alkylation damage to DNA; primarily 1-methyladenine (1mA) and 3-methylcytosine (3mC) lesions created by endogenous or environmental alkylating agents. AlkB is a member of the non-heme iron (II) alpha-ketoglutarate-dependent dioxygenase superfamily
C O Hewitt et al.
Protein engineering, 10(1), 39-44 (1997-01-01)
This paper describes the testing of a homology model of Plasmodium falciparum lactate dehydrogenase (pfLDH) by protein engineering. The model had been validated in structural terms. It suggests explanations of the unusual properties of pfLDH (compared with all other LDHs).
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
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