155-30-6

Usage

Uses

Used in Pharmaceutical Industry:
METHYLMERCAPTO-D-GALACTOPYRANOSIDE is used as an inhibitor for [application type] because of its ability to inhibit glucosidase and β-glucosidase enzymes. This inhibition property makes it a valuable compound in the development of drugs targeting these enzymes, which are involved in various metabolic processes and diseases.
Used in Research and Development:
METHYLMERCAPTO-D-GALACTOPYRANOSIDE is used as a research tool for [application reason] in studies analyzing inducers of the E. coli lac repressor system and investigating the utilization of lactose by Streptococcus faecalis. Its role in these studies helps researchers understand the mechanisms of gene regulation and bacterial metabolism, contributing to the advancement of biological and medical sciences.
Used in Microbiology:
In the field of microbiology, METHYLMERCAPTO-D-GALACTOPYRANOSIDE is used as a substrate for [application type] to study the uptake and metabolism of lactose and glucose by bacteria. The phosphoenolpyruvate-dependent phosphotransferase system maintains the uptake of TMG, lactose, and glucose, providing insights into bacterial nutrient acquisition and energy metabolism.

InChI:InChI=1/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

Upstream product

• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 5188-07-8 sodium thiomethoxide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 40591-65-9 Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-carbamimidoylsulfanyl-tetrahydro-pyran-4-yl ester; hydrobromide 
• 4163-60-4 β-D-galactose peracetate 
• 3908-55-2 Trimethyl(methylthio)silane 

Downstream Products

• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 113421-42-4 methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 113421-41-3 methyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 97205-08-8 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 104992-63-4 Methyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 97205-26-0 methyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 97205-27-1 methyl 2,3-di-O-benzoyl-4,6-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 80667-72-7 methyl 3,6-di-O-benzoyl-1-deoxy-1-thio-β-D-galactopyranoside 
• 80680-55-3 methyl 2,3,6-tri-O-benzoyl-1-deoxy-1-thio-β-D-galactopyranoside 
• 139526-08-2 methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 
• 151072-06-9 methyl 6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 55508-29-7 isopropyl β-D-thiogalactopyranoside 

Relevant academic research and scientific papers

Synthesis of a Novel Analogue of Sialyl Lewis X

Two different strategies have been developed in order to synthesise an analogue and potential mimic of sialyl Lewis X that incorporates a carboxymethyl group and a C2-symmetric 2,3-butanediol unit as replacements for the sialic acid and the N-acetylglucosamine residues respectively.

SYNTHESIS OF THE TETRASACCHARIDE REPEATING UNIT OF THE ANTIGEN FROM KLEBSIELLA TYPE 55

Staring from D-galactose, D-glucose and L-rhamnose, methyl 2-O-acetyl-3-O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside (7) and methyl 2-O-acetyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-O--α-L-rhamnopyranoside (19) have been synthesised.Removal of allyl and benzyl groups from 7 and 19 gave the trisaccharide (9) and the tetrasaccharide repeating unit of the antigen from Klebsiella type 55 in the form of its methyl glycoside (20), respectively.

SYNTHESIS OF A SULFATED GLYCOPEPTIDE CORRESPONDING TO THE CARBOHYDRATE-PROTEIN LINKAGE REGION OF PROTEOGLYCANS: β-D-GlcA-(1->3)4)>-β-D-Gal-(1->3)-β-D-Gal-(1->4)-β-D-Xyl-(1->3)-Ser

A sulfated glycotetraosyl serin 4 was synthesized in a stereocontrolled manner by employing a key glycotetraosyl donor 7 and a serine derivative 6.

Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ1b

The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i. e., 1 (αNeuAc2->8αNeuAc2->3βGal1->4Glc), 2 (αNeuAc2->8αNeuAc2->3Gal), 3 (GalNAc), 4 (αNeuAc2->8NeuAc), 5 (βGal1->3GalNAc), and 42 3βGalNAc1->4(αNeuAc2->3)βGal->4Glc>, is described.All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments.The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary.Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration.Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed.The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAcβ1->4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.

Synthesis of a di-, tri-, and tetra-saccharide unit of the group B streptococcal common antigen.

Condensation of methyl 2,3-O-isopropylidene-alpha-L-rhamnopyranoside with methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside activated by nitrosyl tetrafluoroborate gave an excellent yield of the protected disaccharide 9, which was transformed into glycosyl acceptor 11. Methyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside, obtained from D-galactose penta-acetate and methyl trimethylsilyl sulfide, under catalysis by boron trifluoride etherate, was converted into glycosyl donor 25, which was condensed with 11 under halide-ion catalysis to give the trisaccharide derivative 26. Rhamnosylation with 28 of 27, obtained by selective deprotection of 26, gave the protected tetrasaccharide 29. Deprotection of 10, 26, and 29 gave di- (2), tri- (3) and tetra-saccharide (4) methyl glycosides which form part of the group-specific polysaccharide antigen of Group B Streptococci.

Total synthesis of globotriaosyl-E and Z-ceramides and isoglobotriaosyl-E-ceramide.

Stereoselective, total synthesis of O-alpha-D-galactopyranosyl-(1----4) -O-beta-D-galactopyranosyl-(1----4)-O-beta-D-glucopyranosyl-(1----1)-N -tetracosanoyl-[2S,3R,4E (and 4Z)]-sphingenine and O-alpha-D -galactopyranosyl-(1----3)-O-beta-D-galactopyranosyl-(1----4)-O-beta-D -glucopyranosyl-(1----1)-N-tetracosanoyl-(2S,3R,4E)-sphin gen ine was achieved by using O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate, O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl) -(1----4)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6- tri-O-acetyl-alpha (and beta)-D-glucopyranosyl fluoride, and O-(2,3,4,6-tetra-O-acetyl-alpha-D -galactopyranosyl)-(1----3)-O-(2,3,6-tri-O-acetyl-beta-D-galactopyran osyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate.

LINOMYCIN ANALOGUES. II. CHAIN EXTENSION OF METHYL-6-ALDEHYDO-3,4-O-ISOPROPYLIDENE-1-THIO-β-D-GALACTO-1,5-PYRANOSIDE

Synthesis of methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside and its β-anomer (3 and 4) from the 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide via the isothiouronium salt in HMPT involved a considerable increase in the proportion of the α-anomer.Deacetylation of (3 and 4) with sodium methoxide yielded 5 and 6 respectively.Conversion of 6 into corresponding 3,4-isopropylidene derivative (7) followed by oxidation with Collin reagent gave the aldehydo-sugar (8) which when reacted with the stabilized phosphorane led in the excellent yield to the Z-unsaturated bromo-sugar (9).

A Through-process for the Preparation of Methyl Per-O-acetyl 1-Thio-glycosides from Aldoses

D-Glucose, D-galactose, D-mannose, D-xylose, L-arabinose, L-fucose, L-rhamnose, maltose, cellobiose, lactose, D-glucosamine, D-galactosamine, and D-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.