367-93-1 Usage
Description
IPTG (also known as Isopropyl-β-D-Thiogalactopyranoside) is a molecular biology reagent that functions as an inducer of galactosidase activity by binding to and inhibiting the repressor. It is a molecular mimic of allolactose, a lactose metabolite that triggers transcription of the lac operon, and it is therefore used to induce protein expression where the gene is under the control of the lac operator. IPTG cannot be hydrolyzed or broken down by the E. coli therefore the concentration remains constant during cell replication. IPTG is often used at a final concentration ranging from 0.5-1.0 mM. X-Gal is often used with IPTG since it provides an easy visual method to monitor whether protein expression has occurred. X-Gal as the name implies contains a galactose group that once metabolized causes a bright blue color change.
Chemical Properties
White crystalline powder
Uses
Isopropyl-β-D-thiogalactoside is used as a reagent in molecular biology. It is used as an effective β-galactosidase inducer of protein expression where the gene is under the control of the lac operator. It is used with 5-bromo-4-chloro-3-indolyl-beta-D-galactopyranoside to identify the non-recombinant plasmid in cloning experiments by blue-white screen methodology.
Definition
ChEBI: Isopropyl beta-D-thiogalactopyranoside is an S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.
Application
IPTG (Isopropyl-β-D-thiogalactopyranoside) is a galactose analogue not recognized by β-galactosidase. IPTG is a non-metabolizable galactose analog that induces expression of the lac operon in Escherichia coli. It is a commonly used reagent in cloning procedures that require induction of b-galactosidase activity and is used in conjunction with X-Gal. It is commonly used in cloning procedures that require induction of β-galactosidase activity. It is also used in conjunction with X-Gal or Bluo-Gal in blue-white selection of recombinant bacterial colonies that induce expression of the lac operon in Escherichia coli. IPTG functions by binding to the lacI repressor and altering its conformation, which prevents the repression of the β-galactosidase coding gene lacZ.
Preparation
a synthetic method of isopropyl-β-D-thiogalactoside. The steps are as follows:Step 1: Dissolve β-D-galactose pentaacetate in any organic solvent of methylene chloride, chloroform or 1,2-dichloroethane, and add Lewis acid (boron trifluoride ether, (Aluminum trichloride, zinc chloride) catalyst and potassium ethylxanthate or sodium ethylxanthate are reacted to obtain tetraacetylgalactose ethylxanthate after treatment.Step 2: Dissolve tetraacetyl galactose ethyl xanthate, 2-bromopropane and sodium carbonate in methanol or ethanol at a temperature of 20°C to 80°C and react for 4-6 hours to obtain isopropyl group after treatment Isopropyl-β-D-thiogalactoside.
General Description
Inducer for β-galactosidase, an enzyme that promotes lactose utilization. Use in conjunction with X-Gal. Molecular Biology grade.Stock solutions:X-Gal: 20 mg/ml in DMFIPTG: 20 mg/ml in waterUse 4:1 (X-Gal:IPTG)Assay: ≥99%Dioxane: None detectedMelting point: 110-114°CSpecific rotation [a]25/D (1%, water): -34.0 to -29.0° Intended for laboratory and manufacturing use only. Not for drug, food, or household use.
storage
Store powder at -20°C away from direct sunlight. Once opened and recapped, place container in a low humidity environment at the same storage temperature. Protect from moisture and light by keeping container tightly closed.
Check Digit Verification of cas no
The CAS Registry Mumber 367-93-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 7 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 367-93:
(5*3)+(4*6)+(3*7)+(2*9)+(1*3)=81
81 % 10 = 1
So 367-93-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H18O5S/c1-4(2)15-9-8(13)7(12)6(11)5(3-10)14-9/h4-13H,3H2,1-2H3/t5-,6+,7+,8-,9?/m1/s1
367-93-1Relevant articles and documents
Effect of Photocaged Isopropyl β-d-1-thiogalactopyranoside Solubility on the Light Responsiveness of LacI-controlled Expression Systems in Different Bacteria
Hogenkamp, Fabian,Hilgers, Fabienne,Knapp, Andreas,Klaus, Oliver,Bier, Claus,Binder, Dennis,Jaeger, Karl-Erich,Drepper, Thomas,Pietruszka, J?rg
, p. 539 - 547 (2021)
Photolabile protecting groups play a significant role in controlling biological functions and cellular processes in living cells and tissues, as light offers high spatiotemporal control, is non-invasive as well as easily tuneable. In the recent past, photo-responsive inducer molecules such as 6-nitropiperonyl-caged IPTG (NP-cIPTG) have been used as optochemical tools for Lac repressor-controlled microbial expression systems. To further expand the applicability of the versatile optochemical on-switch, we have investigated whether the modulation of cIPTG water solubility can improve the light responsiveness of appropriate expression systems in bacteria. To this end, we developed two new cIPTG derivatives with different hydrophobicity and demonstrated both an easy applicability for the light-mediated control of gene expression and a simple transferability of this optochemical toolbox to the biotechnologically relevant bacteria Pseudomonas putida and Bacillus subtilis. Notably, the more water-soluble cIPTG derivative proved to be particularly suitable for light-mediated gene expression in these alternative expression hosts.
Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells
Wang, Haoyan,Li, Wei-Guang,Zeng, Kaixing,Wu, Yan-Jiao,Zhang, Yixin,Xu, Tian-Le,Chen, Yiyun
supporting information, p. 561 - 565 (2019/01/04)
The photo-manipulation of bioactive molecules provides unique advantages due to the high temporal and spatial precision of light. The first visible-light uncaging reaction by photocatalytic deboronative hydroxylation in live cells is now demonstrated. Using Fluorescein and Rhodamine derivatives as photocatalysts and ascorbates as reductants, transient hydrogen peroxides were generated from molecular oxygen to uncage phenol, alcohol, and amine functional groups on bioactive molecules in bacteria and mammalian cells, including neurons. This effective visible-light uncaging reaction enabled the light-inducible protein expression, the photo-manipulation of membrane potentials, and the subcellular-specific photo-release of small molecules.
Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)
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, (2018/03/26)
The present invention provides a kind of isopropyl - β - D thio-galactopyranoside synthetic method, namely the method for synthesis of IPTG. Comprises the following steps: five acetyl galactose as raw materials, with the thiourea reaction to obtain the acetyl S - galactose isothiourea fluoro salt, then with the pyrosulfites reaction to obtain the acetyl S - galactose, with isopropyl bromide reaction, the final deacetyl get the compound goal isopropyl - β - D thio-galactopyranoside. In the whole in the reaction process mainly selects the five acetyl galactose and isopropyl bromide as the raw material, not required to be selected smell, toxic isopropyl mercaptan, effectively avoiding harm to human health and the environment, in addition the invention has simple operation, high yield, purity and the like. Is suitable for industrial production. (by machine translation)
