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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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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
Abhishek Chatterjee et al.
Nature chemical biology, 4(12), 758-765 (2008-10-28)
4-Amino-5-hydroxymethyl-2-methylpyrimidine phosphate (HMP-P) synthase catalyzes a complex rearrangement of 5-aminoimidazole ribonucleotide (AIR) to form HMP-P, the pyrimidine moiety of thiamine phosphate. We determined the three-dimensional structures of HMP-P synthase and its complexes with the product HMP-P and a substrate analog
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
Transition State Structure and Inhibition of Rv0091, a 5?-Deoxyadenosine/5?-methylthioadenosine Nucleosidase from Mycobacterium tuberculosis
Namanja-Magliano, HA, et al.
ACS chemical biology, 11(6), 1669-1676 (2016)
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
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