Skip to Content
Merck
CN

D1771

Sigma-Aldrich

5′-Deoxyadenosine

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

Synonym(s):

5′-dAdo

Sign Into View Organizational & Contract Pricing

Select a Size


About This Item

Empirical Formula (Hill Notation):
C10H13N5O3
CAS Number:
Molecular Weight:
251.24
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
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
Identification of a 5?-deoxyadenosine deaminase in Methanocaldococcus jannaschii and its possible role in recycling the radical S-adenosylmethionine enzyme reaction product 5?-deoxyadenosine
Miller D, et al.
Journal of Bacteriology, 196(5), 1064-1072 (2014)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service