D1771
5′-Deoxyadenosine
≥98% (TLC), synthetic (organic), powder
Synonyme(s) :
5′-dAdo
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A propos de cet article
Formule empirique (notation de Hill) :
C10H13N5O3
Numéro CAS:
Poids moléculaire :
251.24
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
MDL number:
Assay:
≥98% (TLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
hot water: 19.60-20.40 mg/mL, clear, colorless
Storage temp.:
2-8°C
Service technique
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5′-Deoxyadenosine, methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase substrate
biological source
synthetic (organic)
Quality Level
assay
≥98% (TLC)
form
powder
solubility
hot water: 19.60-20.40 mg/mL, clear, colorless
storage temp.
2-8°C
SMILES string
C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23
InChI
1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI key
XGYIMTFOTBMPFP-KQYNXXCUSA-N
Application
5′-Deoxyadenosine has been used:
- as a standard in mass spectroscopy
- as an inhibitor for screening thymidine phosphorylase activity
- as a substrate in 5′-Deoxyadenosine deaminase (DadD) assay
Biochem/physiol Actions
5′-Deoxyadenosine is a substrate for the enzyme methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase in microbes. 5′-Deoxyadenosine is a byproduct of cleavage of S-adenosylmethionine (SAM). High levels of 5′-Deoxyadenosine inhibits SAM dependent enzymes. It also inhibits biotin synthase (BioB) and lipoyl synthase (LipA) enzymes.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Charles J Walsby et al.
Inorganic chemistry, 44(4), 727-741 (2005-04-30)
Electron paramagnetic resonance (EPR), electron-nuclear double resonance (ENDOR), and Mössbauer spectroscopies and other physical methods have provided important new insights into the radical-SAM superfamily of proteins, which use iron-sulfur clusters and S-adenosylmethionine to initiate H atom abstraction reactions. This remarkable
The nucleoside derivative 5?-O-trityl-inosine (KIN59) suppresses thymidine phosphorylase-triggered angiogenesis via a noncompetitive mechanism of action
Liekens S, et al.
Test, 279(28), 29598-29605 (2004)
Kenichi Yokoyama et al.
Biochemistry, 47(34), 8950-8960 (2008-08-05)
BtrN is a radical SAM ( S-adenosyl- l-methionine) enzyme that catalyzes the oxidation of 2-deoxy- scyllo-inosamine (DOIA) into 3-amino-2,3-dideoxy- scyllo-inosose (amino-DOI) during the biosynthesis of 2-deoxystreptamine (DOS) in the butirosin producer Bacillus circulans. Recently, we have shown that BtrN catalyzes