T9567
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:
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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