M8146

Methyl-β-D-thiogalactoside

Name: Methyl-β-<SC>D</SC>-thiogalactoside
Brand: SIGMA

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₇H₁₄O₅S

CAS Number:

155-30-6

Molecular Weight:

210.25

UNSPSC Code:

12352201

NACRES:

NA.25

PubChem Substance ID:

24897226

EC Number:

205-842-4

Beilstein/REAXYS Number:

81583

MDL number:

MFCD00038073

InChI key

LZFNFLTVAMOOPJ-PZRMXXKTSA-N

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

SMILES string

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

biological source

synthetic

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

Quality Level

200

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Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

Chemistry & Biochemicals

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.

General description

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

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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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)

Analysis of inducers of the E.coli lac repressor system in mammalian cells and whole animals.

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

Arginine binding motifs: design and synthesis of galactose-derived arginine tweezers as galectin-3 inhibitors.

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

Phosphorylation of HPr by the bifunctional HPr Kinase/P-ser-HPr phosphatase from Lactobacillus casei controls catabolite repression and inducer exclusion but not inducer expulsion.

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

Regulation of the glucose:H+ symporter by metabolite-activated ATP-dependent phosphorylation of HPr in Lactobacillus brevis.

J J Ye et al.

Journal of bacteriology, 176(12), 3484-3492 (1994-06-01)

Lactobacillus brevis takes up glucose and the nonmetabolizable glucose analog 2-deoxyglucose (2DG), as well as lactose and the nonmetabolizable lactose analoge thiomethyl beta-galactoside (TMG), via proton symport. Our earlier studies showed that TMG, previously accumulated in L. brevis cells via

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