19165-11-8

Usage

Uses

Used in Molecular Biology Research:
ISOPROPYL BETA-D-THIOGLUCOPYRANOSIDE is used as an inducer of protein expression for the activation of the Lac operon in bacteria. This allows for the controlled expression of genes of interest, facilitating the study and production of specific proteins.
Used in Genetic Engineering:
ISOPROPYL BETA-D-THIOGLUCOPYRANOSIDE is used as a tool in genetic engineering to regulate the expression of inserted genes. By controlling the activation of the Lac operon, researchers can manipulate the production of recombinant proteins, enabling the development of genetically modified organisms with desired traits.
Used in Laboratory Settings:
ISOPROPYL BETA-D-THIOGLUCOPYRANOSIDE is used as a stable and non-toxic alternative to other inducers in laboratory experiments. Its properties make it suitable for a wide range of applications, including the study of gene regulation, protein function, and the development of new biotechnological products.

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

Upstream product

• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 55692-84-7 isopropyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 631919-01-2 allyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-di-O-benzoyl-α-D-mannopyranoside 
• 183368-32-3 1-isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 1307870-93-4 C₂₅H₃₄O₇S 
• 1307870-88-7 C₄₉H₆₉NO₉ 

Relevant academic research and scientific papers

One-Pot Relay Glycosylation

A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.

A practical synthesis of α-D-Manp-(1→3)-α-D-Manp- (1→2)-[α-D-Glcp-(1→3)]-α-D-Manp-(1→2) -α-D-Manp-(1→2)-α-D-Manp, an O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c

An O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c, α-D-Manp-(1→3)-α-D-Manp-(1→2)-[α-D-Glcp- (1→3)]-α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp was synthesized as its methyl glycoside. Acetylation of allyl 4,6-O-benzylidene-α-D-mannopyranoside, followed by debenzylidenization and benzoylation gave allyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-α-D- mannopyranoside (3), and subsequent deacetylation of 3 with CH 3COCl-MeOH gave the monosaccharide acceptor 4. Condensation of isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (6) with 4 selectively afforded the α-(1→3)-linked disaccharide 7. Condensation of 7 with the (1→3)-linked disaccharide donor 9, followed by deallylation and trichloroacetimidation, afforded the tetrasaccharide donor 12. Coupling of 12 with disaccharide acceptor 13, followed by debenzylation and deacylation, furnished the target heterohexasaccharide 16.

Glycosylimidates, 8. - Synthesis of 1-Thioglycosides

As expected, the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration.The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides.The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.