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D1771

Sigma-Aldrich

5′-Deoxyadenosine

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

Synonym(s):

5′-dAdo

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About This Item

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.

Storage Class Code

11 - Combustible Solids

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)

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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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)
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
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
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