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Merck
CN

T9567

Sigma-Aldrich

Thiolactomycin

98% (HPLC), solid

Synonym(s):

(5R)-4-Hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadienyl]-2(5H)-thiophenone, Antibiotic 2-200, [R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone

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About This Item

Empirical Formula (Hill Notation):
C11H14O2S
CAS Number:
Molecular Weight:
210.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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Assay

98% (HPLC)

form

solid

color

light yellow

solubility

DMSO: soluble ~21 mg/mL
H2O: insoluble

SMILES string

C\C(C=C)=C/[C@@]1(C)SC(=O)C(C)=C1O

Gene Information

human ... FASN(2194)

Biochem/physiol Actions

Inhibitor of bacterial myristate synthesis. Does not inhibit eukaryotic myristate synthesis; antibiotic; antitrypanosomal. Shown to be effective against human sleeping sickness parasite, Trypanosoma brucei, as well as malaria parasite and toxoplasma.

Storage Class Code

13 - Non 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

Regulatory Information

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Veemal Bhowruth et al.
Bioorganic & medicinal chemistry letters, 17(20), 5643-5646 (2007-09-04)
Fifteen novel C5 analogues of thiolactomycin (13 biphenyl analogues and two biphenyl mimics) have been synthesised and assessed for their in vitro mtFabH and whole cell Mycobacterium bovis BCG activity, respectively. Analysis of the 15 compounds revealed that six possessed
Xin He et al.
Antimicrobial agents and chemotherapy, 48(8), 3093-3102 (2004-07-27)
The enzyme FabH catalyzes the initial step of fatty acid biosynthesis via a type II dissociated fatty acid synthase. The pivotal role of this essential enzyme, combined with its unique structural features and ubiquitous occurrence in bacteria, has made it
Variable synthesis of the optically active thiotetronic acid antibiotics thiolactomycin, thiotetromycin, and 834-B1.
Korinna L Dormann et al.
Angewandte Chemie (International ed. in English), 46(7), 1160-1163 (2006-12-22)
Pilho Kim et al.
Journal of medicinal chemistry, 49(1), 159-171 (2006-01-06)
Thiolactomycin inhibits bacterial cell growth through inhibition of the beta-ketoacyl-ACP synthase activity of type II fatty acid synthases. The effect of modifications of the 5-position isoprenoid side chain on both IC(50) and MIC were determined. Synthesis and screening of a
Sylvia R Luckner et al.
Structure (London, England : 1993), 17(7), 1004-1013 (2009-07-17)
Mycobacteria have a unique cell wall consisting of mycolic acids, very-long-chain lipids that provide protection and allow the bacteria to persist within human macrophages. Inhibition of cell wall biosynthesis is fatal for the organism and a starting point for the

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