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D1771

Sigma-Aldrich

5′-Deoxyadenosine

methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase substrate

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Synonym(s):
5′-dAdo
Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
4754-39-6
Molecular Weight:
251.24
MDL number:
MFCD00056003
UNSPSC Code:
41106305
PubChem Substance ID:
24893539
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

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

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Gunhild Layer et al.
Current opinion in chemical biology, 8(5), 468-476 (2004-09-29)
'Radical SAM' enzymes juxtapose a [4Fe-4S] cluster and S-adenosyl-l-methionine (SAM) to generate catalytic 5'-deoxyadenosyl radicals. The crystal structures of oxygen-independent coproporphyrinogen III oxidase HemN and biotin synthase reveal the positioning of both cofactors with respect to each other and relative
Joseph T Jarrett
Current opinion in chemical biology, 7(2), 174-182 (2003-04-26)
Adenosylmethionine-dependent radical enzymes provide a novel mechanism for generating the highly oxidizing 5'-deoxyadenosyl radical in an anaerobic reducing environment. Recent studies suggest a unique covalent interaction between adenosylmethionine and a catalytic iron-sulfur cluster that may promote inner-sphere electron transfer to
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)
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