scholarly journals Derivatization of Oligosaccharides from Glycosphingolipids with Aminobenzoic Acid Ethyl Ester and Analysis of Saccharide Structure of Glycosphingolipids by Two-Dimensional Mapping with High Performance Liquid Chromatography

1990 ◽  
Vol 2 (8) ◽  
pp. 514-519 ◽  
Author(s):  
Hideyoshi HIGASHI
Author(s):  
Tatiana G. Volkova ◽  
Irina O. Talanova

The problem of obtaining highly soluble and biologically active drugs is actual. One of the methods for solving this problem is the inclusion of carbohydrate residues into the structure of biologically active compounds. Ethyl ester of p-(N-α-D-glucopyranoside)aminobenzoic acid has been synthesized by condensation of benzocaine with glucose. The obtained product has been studied by means of NMR spectroscopy, high-performance liquid chromatography and elemental analysis. Comparative analysis of the lipophilic properties of benzocaine and its glycosylated analogue and a profile of the potential target-specific activity of the latter has also been carried out. According to high-performance liquid chromatography data the obtained product was a mixture of the initial benzocaine and its glycosylated analogue with a content of components of 30% and 68.5%, respectively. It was shown that the inclusion of glucose fragment into the structure of benzocaine led to the decrease in the value of the lipophilicity coefficient and the increase in its solubility in water. A significant difference in the solubility of benzocaine and its glycosylated analogue was proved by NMR data. It was used for their separation, i.e. benzocaine was removed from the mixture by dissolving in chloroform. Virtual screening was carried out and a profile of the potential bioactivity of glycosylated benzocaine was obtained. It has been noted that ethyl ester of p-(N-α-D-glucopyranoside)aminobenzoic acid would participate in the metabolism of carbohydrates, amino acids and lipids.Forcitation:Volkova T.G., Talanova I.O. Synthesis and study of water soluble forms of anaesthesin. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2018. V. 61. N 6. P. 35-40


Lab on a Chip ◽  
2016 ◽  
Vol 16 (24) ◽  
pp. 4648-4652 ◽  
Author(s):  
Carsten Lotter ◽  
Elisabeth Poehler ◽  
Josef J. Heiland ◽  
Laura Mauritz ◽  
Detlev Belder

Chip-integrated, two-dimensional high performance liquid chromatography is introduced to monitor enantioselective continuous micro-flow synthesis.


Sign in / Sign up

Export Citation Format

Share Document