Regioselective deprotection of the monosaccharide-bearing thiocyanomethyl group at the anomeric position monitored by reversed-phase HPLC method
| Autor: | Khaldun M. Al Azzam, Qais Abualassal, Jamal A. Jilani |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Pharmacology
chemistry.chemical_classification Chromatography Anomer Immobilized enzyme biology 010405 organic chemistry Clinical Biochemistry General Medicine 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Analytical Chemistry Hydrolysis Column chromatography chemistry Biocatalysis Enzymatic hydrolysis Drug Discovery biology.protein Monosaccharide Organic chemistry Lipase Molecular Biology |
| Zdroj: | Biomedical Chromatography. 30:1416-1422 |
| ISSN: | 0269-3879 |
| DOI: | 10.1002/bmc.3699 |
| Popis: | In the current work, the investigation and development of a chemo-enzymatic approach for the synthesis of neo-glycoproteins have been studied. This strategy is based on the regioselective enzymatic hydrolysis of peracetylated monosaccharide, functionalized at the anomeric position (C1) as 1-thio-(S-cyanomethyl) group, a precursor of the 2- iminomethoxyethyl thioglycosides-linker for protein glycosylation, catalyzed by immobilized enzymes to obtain selectively monodeprotected compounds. The use of this activation in C1 is the most frequently used strategy for glycoprotein preparation. The selected biocatalysts are the lipase from Candida rugosa and the acetyl xylan esterase from Bacillus pumilus. A reversed-phase high-performance liquid-chromatographic (HPLC) method for monitoring the regioselective deprotection reaction has been developed. The developed HPLC method was used as a fingerprint to follow the hydrolysis of substrate 1 to substrate 1a and to determine its purity and yield. Moreover, the obtained compound was further purified by flash chromatography. The obtained compound 1a was further characterized using (1) H, (13) C NMR, correlation spectroscopy (COSY) and heteronuclear multiple bond correlation. The resulting product can be used as an intermediate for the preparation of di- and more complex oligosaccharides aimed at protein conjugation. Copyright © 2016 John Wiley & Sons, Ltd. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text