168037-40-9

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 
• 22352-19-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate 

Relevant academic research and scientific papers

Glycoconjugated Porphyrins. 3. Synthesis of Flat Amphiphilic Mixed meso-(Glycosylated aryl)porphyrins and Mixed meso-(Glycosylated aryl)alkylporphyrins Bearing Some Mono- and Disaccharide Groups

p-Acetylglycosylated benzaldehydes react with pyrrole by Lindsey's method to produce a variety of flat glycosylated porphyrins.By the same method a large series of amphiphilic mixed glycosylated arylaryl- and mixed glycosylated arylalkylporphyrins have been synthesized, using pyrrole, p-acetylglycosylated benzaldehyde and aryl aldehyde or alkyl aldehyde as starting materials.Under optimized conditions, the di- or teiglycosylated derivatives were principally obtained whereas the formation of meso tetrasubstituted porphyrins is minimized.Deprotection of acetyl glycoside moieties allows us to obtain products with good solubility in neutral aqueous solution and a wide range of amphiphilic character.The structure of these new protected and unprotected compounds in solution was confirmed by 1H NMR studies.

Potential Dental Biofilm Inhibitors: Dynamic Combinatorial Chemistry Affords Sugar-Based Molecules that Target Bacterial Glucosyltransferase

We applied dynamic combinatorial chemistry (DCC) to find novel ligands of the bacterial virulence factor glucosyltransferase (GTF) 180. GTFs are the major producers of extracellular polysaccharides, which are important factors in the initiation and development of cariogenic dental biofilms. Following a structure-based strategy, we designed a series of 36 glucose- and maltose-based acylhydrazones as substrate mimics. Synthesis of the required mono- and disaccharide-based aldehydes set the stage for DCC experiments. Analysis of the dynamic combinatorial libraries (DCLs) by UPLC-MS revealed major amplification of four compounds in the presence of GTF180. Moreover, we found that derivatives of the glucose-acceptor maltose at the C1-hydroxy group act as glucose-donors and are cleaved by GTF180. The synthesized hits display medium to low binding affinity (KD values of 0.4–10.0 mm) according to surface plasmon resonance. In addition, they were investigated for inhibitory activity in GTF-activity assays. The early-stage DCC study reveals that careful design of DCLs opens up easy access to a broad class of novel compounds that can be developed further as potential inhibitors.

Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid - Ac2O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins. Trisalkylpyridinium porphyrins substituted by one glycosyl (glucosyl, maltosyl, and lactosyl) moiety have been prepared in acceptable yields. These glycosylated cationic porphyrins have been synthesized from pyrrole condensed with 4-pyridinecarboxaldehyde, and suitable ortho- or para peracetylglycosyloxybenzaldehyde derivatives in refluxing propionic acid - Ac2O followed by action of alkyliodide in DMF. Deprotection of the glycosylated moieties led to a new class of representative glycosylated porphyrins.