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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

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Certificates of Analysis (COA)

Lot/Batch Number
109K1044

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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
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
H H Saxild et al.
Journal of bacteriology, 176(2), 276-283 (1994-01-01)
Random genomic Bacillus subtilis lacZ fusions were screened in order to identify the possible existence of regulons responding to the stimuli generated by partial purine starvation. A leaky pur mutation (purL8) was isolated and used to generate the partial purine
Shigeo Tojo et al.
Journal of bacteriology, 190(18), 6134-6147 (2008-07-22)
Branched-chain amino acids are the most abundant amino acids in proteins. The Bacillus subtilis ilv-leu operon is involved in the biosynthesis of branched-chain amino acids. This operon exhibits a RelA-dependent positive stringent response to amino acid starvation. We investigated this
T Msadek et al.
Journal of bacteriology, 173(7), 2366-2377 (1991-04-01)
Production of a class of both secreted and intracellular degradative enzymes in Bacillus subtilis is regulated at the transcriptional level by a signal transduction pathway which includes the DegS-DegU two-component system and at least two additional regulatory genes, degQ and
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