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N5131

Sigma-Aldrich

Nicotinamide guanine dinucleotide sodium salt

phospodiesterase and ADP-ribosyl cyclase substrate

Synonym(s):

3-(Aminocarbonyl)-1-[(2R,3R,4S,5R)-5-({[(S)-{[(S)-{[(2R,3S,4R,5R)-5-(2-Amino-6-Oxo-1,6-Dihydro-9h-Purin-9-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy} (Hydroxy)phosphoryl]ox, NGD

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About This Item

Empirical Formula (Hill Notation):
C21H28N7O15P2
CAS Number:
5624-35-1
Molecular Weight:
680.43
MDL number:
MFCD00079505
UNSPSC Code:
41106305
PubChem Substance ID:
24897721
NACRES:
NA.51

form

powder

storage temp.

−20°C

SMILES string

NC(=O)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5C(=O)N=C(N)Nc45)C(O)C2O

InChI

1S/C21H28N7O15P2/c22-16(33)8-2-1-3-27(4-8)19-14(31)12(29)9(41-19)5-39-44(35,36)43-45(37,38)40-6-10-13(30)15(32)20(42-10)28-7-24-11-17(28)25-21(23)26-18(11)34/h1-4,7,9-10,12-15,19-20,29-32H,5-6H2,(H2,22,33)(H,35,36)(H,37,38)(H3,23,25,26,34)

InChI key

WWXCUPZEUROLRY-UHFFFAOYSA-N

Application

Nicotinamide guanine dinucleotide (NGD+) may be used as a preferred substrate of specific snake Trimeresurus stejnegeri venom phospodiesterase and a substrate to study the specificity and kinetics of ADP-ribosyl cyclase(s).
Nicotinamide guanine dinucleotide sodium salt has been used as a substrate for measuring the cyclase activity of the enzyme cluster of differentiation 38 (CD38). It has also been used as a substrate to fluorometrically determine the activity of CD38/ADP-ribose (ADPR).

Biochem/physiol Actions

Nicotinamide guanine dinucleotide sodium salt is used to determine the activity of proteins that generate cyclic-ADP-ribose (cADPR) in the ADP-ribosyl cyclase family.

Other Notes

Analog of β-NAD

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Andrea Fabiano et al.
Visual neuroscience, 28(2), 121-128 (2011-01-29)
Cyclic ADP-ribose (cADPR) is a second messenger modulating intracellular calcium levels. We have previously described a cADPR-dependent calcium signaling pathway in bovine rod outer segments (ROS), where calcium ions play a pivotal role. ROS ADP-ribosyl cyclase (ADPR-cyclase) was localized in
M E Migaud et al.
Biochemistry, 38(28), 9105-9114 (1999-07-22)
Readily synthesized nicotinamide adenine dinucleotide (NAD(+)) analogues have been used to investigate aspects of the cyclization of NAD(+) to cyclic adenosine 5'-O-diphosphate ribose (cADPR) catalyzed by the enzyme adenosine 5'-O-diphosphate (ADP) ribosyl cyclase and to produce the first potent inhibitors
M Liang et al.
Archives of biochemistry and biophysics, 371(2), 317-325 (1999-11-05)
Here we investigated whether cADPR and NAADP are synthesized in mitochondria. We found that ADPR-cyclase activity is present in mitochondria. In addition, we describe for the first time synthesis of NAADP in this intracellular organelle. ADPR-cyclase activities (V(MAX)) and NAADP
L G Mészáros et al.
Biochemical and biophysical research communications, 234(1), 252-256 (1997-05-08)
Two types of ADP-ribosyl cyclase activity were distinguished in dog and rat cardiac muscles by measuring the enzymatic conversion of NGD (as an NAD analog) into the fluorescent product cyclic GDP-ribose in cardiac muscle subcellular fractions. Both types of activity
C Munshi et al.
Biochimica et biophysica acta, 1388(2), 428-436 (1998-12-22)
ADP-ribosyl cyclase is a multi-functional enzyme that catalyzes the formation of two Ca2+ signaling molecules, cyclic ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide phosphate (NAADP). X-ray crystallography of three different crystal forms shows that it is a non-covalent dimer. Chemical
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