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M8146

Sigma-Aldrich

Methyl-β-D-thiogalactoside

Synonym(s):

Methyl-1-thio-β-D-galactopyranoside, TMG

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About This Item

Empirical Formula (Hill Notation):
C7H14O5S
CAS Number:
Molecular Weight:
210.25
Beilstein:
81583
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic

Quality Level

Assay

≥98% (TLC)

form

powder

technique(s)

thin layer chromatography (TLC): suitable

color

white

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CS[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

InChI

1S/C7H14O5S/c1-13-7-6(11)5(10)4(9)3(2-8)12-7/h3-11H,2H2,1H3/t3-,4+,5+,6-,7+/m1/s1

InChI key

LZFNFLTVAMOOPJ-PZRMXXKTSA-N

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General description

The uptake of methyl-β-D-thiogalactoside (TMG), lactose, and glucose is maintained by the phosphoenolpyruvate-dependent phosphotransferase system.

Application

Methyl-β-D-thiogalactoside has been used in a study to analyze inducers of the E.coli lac repressor system. It has also been used in a study that investigated the utilization of lactose by Streptococcus faecalis.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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β-D-phosphogalactoside galactohydrolase of Streptococcus faecalis and the inhibition of its synthesis by glucose
Heller, K. and R. Roschenthaler
Canadian Journal of Microbiology, 24, 512-519 (1979)
D L Wyborski et al.
Nucleic acids research, 19(17), 4647-4653 (1991-09-11)
Although the inducible prokaryotic lac repressor system has been successfully adapted for control of gene expression in mammalian cells, little information is available on the pharmacokinetics of beta-galactoside inducers in mammalian cells for optimizing this system. These studies directly measure
Christopher T Oberg et al.
Journal of medicinal chemistry, 51(7), 2297-2301 (2008-03-06)
Anionic O2 derivatives of methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta-D-galactopyranoside have been synthesized as inhibitors against galectin-3. The sulfate, H-phosphonate, and benzyl phosphate derivatives showed an increased affinity as compared to the parent unsubstituted galactopyranoside. Modeling revealed arginine-144 being pinched by the C3 benzamide
V Dossonnet et al.
Journal of bacteriology, 182(9), 2582-2590 (2000-04-13)
We have cloned and sequenced the Lactobacillus casei hprK gene encoding the bifunctional enzyme HPr kinase/P-Ser-HPr phosphatase (HprK/P). Purified recombinant L. casei HprK/P catalyzes the ATP-dependent phosphorylation of HPr, a phosphocarrier protein of the phosphoenolpyruvate:carbohydrate phosphotransferase system at the regulatory
J J Ye et al.
The Journal of biological chemistry, 269(16), 11837-11844 (1994-04-22)
Lactococcus lactis takes up lactose and the nonmetabolizable lactose analogue, thiomethyl-beta-galactoside (TMG), via the phosphoenolpyruvate:sugar phosphotransferase system (PTS) which couples sugar transport to sugar phosphorylation. Earlier studies had shown that TMG-phosphate, previously accumulated in L. lactis cells, is rapidly dephosphorylated

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