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D1071

Sigma-Aldrich

Decoyinine

Synonym(s):

9-(6-Deoxy-D-β-erythro-hex-5-en-2-ulofuranosyl)adenine

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About This Item

Empirical Formula (Hill Notation):
C11H13N5O4
CAS Number:
2004-04-8
Molecular Weight:
279.25
UNSPSC Code:
51101500
PubChem Substance ID:
329798669

form

solid

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

Nc1ncnc2n(cnc12)[C@]3(CO)OC(=C)[C@@H](O)[C@H]3O

InChI

1S/C11H13N5O4/c1-5-7(18)8(19)11(2-17,20-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-4,7-8,17-19H,1-2H2,(H2,12,13,14)/t7-,8-,11-/m1/s1

InChI key

UZSSGAOAYPICBZ-SOCHQFKDSA-N

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Application

Decoyinine is used to study the inhibition of cell wall synthesis, to inhibit RNA synthesis, to lower intracellular GTP levels in Streptococcus mutans, and to initiate sporulation in Bacillus.

Biochem/physiol Actions

Decoyinine is a Xanthosine monophosphate (XMP) aminase inhibitor and GMP synthetase inhibitor.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Jennifer Mobberley et al.
Applied and environmental microbiology, 76(3), 829-842 (2009-12-17)
Eleven Bacillus isolates from the surface and subsurface waters of the Gulf of Mexico were examined for their capacity to sporulate and harbor prophages. Occurrence of sporulation in each isolate was assessed through decoyinine induction, and putative lysogens were identified
S Yamashita et al.
Journal of general microbiology, 135(5), 1335-1345 (1989-05-01)
The expression of the spo0A-lacZ fusion gene was partially repressed in the presence of an excess of glucose. Expression was restored either by the mutation sigA47(crsA47) or by addition of decoyinine, an inhibitor of GMP synthetase, to the medium. By
José A Lemos et al.
Journal of bacteriology, 190(15), 5291-5299 (2008-06-10)
The RelA, RelP, and RelQ enzymes are responsible for the production of the alarmone (p)ppGpp in Streptococcus mutans. A strain lacking all three synthetases (DeltarelAPQ) does not grow in minimal medium lacking the branched-chain amino acids (BCAA) leucine or valine
P G Andreis et al.
International journal of molecular medicine, 3(1), 59-62 (1998-12-29)
Guanylin is a 15-amino acid peptide, which activates guanylate cyclase (GC) and plays a major role in the regulation of water and electrolyte secretion by intestinal mucosa. The expression of guanylin prohormone has been recently demonstrated in the rat adrenal
T Maruyama et al.
Nucleic acids symposium series, (25)(25), 87-88 (1991-01-01)
9-Cyclobutyladenines bearing both methylene and hydroxymethyl groups, 3 and 4, were prepared by dehydration of carbocyclic oxetanocin A, 1a. Introduction of a double bond into cyclobutane ring was achieved by allylic oxidation of 12, which after several steps, afforded 5.
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