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D1771

5′-Deoxyadenosine

Name: 5&#8242;-Deoxyadenosine
Brand: SIGMA

≥98% (TLC), synthetic (organic), powder

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

UNSPSC Code:

41106305

PubChem Substance ID:

24893539

NACRES:

NA.51

MDL number:

MFCD00056003

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

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Product Name

5′-Deoxyadenosine, methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase substrate

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

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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Characterization and mechanistic study of a radical SAM dehydrogenase in the biosynthesis of butirosin.

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

The PLP-dependent biotin synthase from Escherichia coli: mechanistic studies.

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

Spectroscopic approaches to elucidating novel iron-sulfur chemistry in the "radical-Sam" protein superfamily.

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)

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)

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Global Trade Item Number

SKU	GTIN
D1771-25MG	04061833560723

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