D1771
5′-Deoxyadenosine
≥98% (TLC), synthetic (organic), powder
Synonym(s):
5′-dAdo
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About This Item
Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
Molecular Weight:
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
Product Name
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.
Storage Class
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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Kenichi Yokoyama et al.
Journal of the American Chemical Society, 129(49), 15147-15155 (2007-11-16)
BtrN encoded in the butirosin biosynthetic gene cluster possesses a CXXXCXXC motif conserved within the radical S-adenosyl methionine (SAM) superfamily. Its gene disruption in the butirosin producer Bacillus circulans caused the interruption of the biosynthetic pathway between 2-deoxy-scyllo-inosamine (DOIA) and
Sandrine Ollagnier-de-Choudens et al.
FEBS letters, 532(3), 465-468 (2002-12-17)
Biotin synthase (BioB), an iron-sulfur enzyme, catalyzes the last step of the biotin biosynthesis pathway. The reaction consists in the introduction of a sulfur atom into two non-activated C-H bonds of dethiobiotin. Substrate radical activation is initiated by the reductive
Alhosna Benjdia et al.
Journal of the American Chemical Society, 131(24), 8348-8349 (2009-06-06)
Sulfatases are unique in requiring an essential post-translational modification of a critical active-site cysteinyl or seryl residue to 3-oxoalanine usually called C alpha-formylglycine (FGly). This post-translational modification is catalyzed anaerobically by anaerobic Sulfatase Maturating Enzyme (anSME), a member of the