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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)

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K Ochi
Journal of bacteriology, 169(8), 3608-3616 (1987-08-01)
I investigated the significance of the intracellular accumulation of guanosine 5'-diphosphate 3'-diphosphate (ppGpp) and of the coordinated decrease in the GTP pool for initiating morphological and physiological differentiation of Streptomyces griseus, a streptomycin-producing strain. In solid cultures, aerial mycelium formation
F J Slack et al.
Molecular microbiology, 5(8), 1915-1925 (1991-08-01)
The Bacillus subtilis dciA operon, which encodes a dipeptide transport system, was induced rapidly by several conditions that caused the cells to enter stationary phase and initiate sporulation. The in vivo start point of transcription was mapped precisely and shown
A Fouet et al.
Journal of bacteriology, 172(2), 835-844 (1990-02-01)
Expression of the aconitase (citB) gene of Bacillus subtilis is subject to catabolite repression in cells grown in minimal media. In nutrient broth medium, citB expression is low in growing cells but is induced when cells enter sporulation. A 600-base-pair
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
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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