Cargando…
Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method
Purpose: To describe a chemoenzymatic approach joining an enzymatic regioselective hydrolysis of peracetylated N-acetyl-α-D-glucosamine (A) with a mild controlled acyl relocation which resulted 2-acetamido-2 deoxy-1,3,6-tri-O-acetyl-α-D-glucopyranose (1B). Methods: Immobilization of lipase on decaoc...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Tabriz University of Medical Sciences
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5527246/ https://www.ncbi.nlm.nih.gov/pubmed/28761834 http://dx.doi.org/10.15171/apb.2017.037 |
_version_ | 1783252940773916672 |
---|---|
author | Abualassal, Qais Ibrahim Al Azzam, Khaldun Mohammad Abudayeh, Zead Helmi Hassouneh, Loay Khaled |
author_facet | Abualassal, Qais Ibrahim Al Azzam, Khaldun Mohammad Abudayeh, Zead Helmi Hassouneh, Loay Khaled |
author_sort | Abualassal, Qais Ibrahim |
collection | PubMed |
description | Purpose: To describe a chemoenzymatic approach joining an enzymatic regioselective hydrolysis of peracetylated N-acetyl-α-D-glucosamine (A) with a mild controlled acyl relocation which resulted 2-acetamido-2 deoxy-1,3,6-tri-O-acetyl-α-D-glucopyranose (1B). Methods: Immobilization of lipase on decaoctyl (DSEOD) and octyl-agarose (OSCL) was carried out as reported by the work of Bastida et al. The newly developed RP-HPLC method for examining the enzymatic hydrolysis was carried out isocratically utilizing a HPLC system. Results: The new approach resulted the target compound (B) in 95% yield after purification utilizing flash column chromatography. Candida rugosa-lipase immobilized ondecaoctyl-sepabeads was the best catalyst in terms of activity and region-selectivity in the hydrolysis of substrate (A), delivering the deacetylation at C6 position (98% general yield). Also, a reversed-phase high-performance liquid-chromatographic (RP-HPLC) method for controlling the region-selective hydrolysis of peracetylated N-acetyl-α-D-glucosamine (A) with a mild monitored acyl movement which led to 2-acetamido-2-deoxy-1,3,6-tri-O-acetyl-α-D-glucopyranose (1B) has additionally been developed. The developed RP-HPLC method was utilized as fingerprints to follow the hydrolysis of substrate (A) and to determine its purity and additionally yield. Furthermore, the acquired compound (B) was further purified by flash chromatography. Compound (B) was further characterized utilizing (1)HNMR and mass spectrometry. Conclusion: An efficient chemoenzymatic procedure to optimize the preparation of peracetylated lactosamine B containing acetyl ester as extraordinary protecting group is presented. Compound B is a significant intermediate for the synthesis of pharmacologically active compound (e.g. complex oligosaccharides for biochemical, biophysical, or biological examinations). Besides, reaction monitoring utilizing HPLC proposes more exact information than spectroscopic methods. |
format | Online Article Text |
id | pubmed-5527246 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Tabriz University of Medical Sciences |
record_format | MEDLINE/PubMed |
spelling | pubmed-55272462017-07-31 Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method Abualassal, Qais Ibrahim Al Azzam, Khaldun Mohammad Abudayeh, Zead Helmi Hassouneh, Loay Khaled Adv Pharm Bull Research Article Purpose: To describe a chemoenzymatic approach joining an enzymatic regioselective hydrolysis of peracetylated N-acetyl-α-D-glucosamine (A) with a mild controlled acyl relocation which resulted 2-acetamido-2 deoxy-1,3,6-tri-O-acetyl-α-D-glucopyranose (1B). Methods: Immobilization of lipase on decaoctyl (DSEOD) and octyl-agarose (OSCL) was carried out as reported by the work of Bastida et al. The newly developed RP-HPLC method for examining the enzymatic hydrolysis was carried out isocratically utilizing a HPLC system. Results: The new approach resulted the target compound (B) in 95% yield after purification utilizing flash column chromatography. Candida rugosa-lipase immobilized ondecaoctyl-sepabeads was the best catalyst in terms of activity and region-selectivity in the hydrolysis of substrate (A), delivering the deacetylation at C6 position (98% general yield). Also, a reversed-phase high-performance liquid-chromatographic (RP-HPLC) method for controlling the region-selective hydrolysis of peracetylated N-acetyl-α-D-glucosamine (A) with a mild monitored acyl movement which led to 2-acetamido-2-deoxy-1,3,6-tri-O-acetyl-α-D-glucopyranose (1B) has additionally been developed. The developed RP-HPLC method was utilized as fingerprints to follow the hydrolysis of substrate (A) and to determine its purity and additionally yield. Furthermore, the acquired compound (B) was further purified by flash chromatography. Compound (B) was further characterized utilizing (1)HNMR and mass spectrometry. Conclusion: An efficient chemoenzymatic procedure to optimize the preparation of peracetylated lactosamine B containing acetyl ester as extraordinary protecting group is presented. Compound B is a significant intermediate for the synthesis of pharmacologically active compound (e.g. complex oligosaccharides for biochemical, biophysical, or biological examinations). Besides, reaction monitoring utilizing HPLC proposes more exact information than spectroscopic methods. Tabriz University of Medical Sciences 2017-06 2017-06-30 /pmc/articles/PMC5527246/ /pubmed/28761834 http://dx.doi.org/10.15171/apb.2017.037 Text en ©2017 The Authors. http://creativecommons.org/licenses/by/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution (CC BY), which permits unrestricted use, distribution, and reproduction in any medium, as long as the original authors and source are cited. No permission is required from the authors or the publishers. |
spellingShingle | Research Article Abualassal, Qais Ibrahim Al Azzam, Khaldun Mohammad Abudayeh, Zead Helmi Hassouneh, Loay Khaled Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title | Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title_full | Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title_fullStr | Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title_full_unstemmed | Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title_short | Development and Optimization of a New Chemoenzymatic Approach for the Synthesis of Peracetylated Lactosamine (Intermediate for the Synthesis of Pharmacologically Active Compounds) Monitored by RP- HPLC Method |
title_sort | development and optimization of a new chemoenzymatic approach for the synthesis of peracetylated lactosamine (intermediate for the synthesis of pharmacologically active compounds) monitored by rp- hplc method |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5527246/ https://www.ncbi.nlm.nih.gov/pubmed/28761834 http://dx.doi.org/10.15171/apb.2017.037 |
work_keys_str_mv | AT abualassalqaisibrahim developmentandoptimizationofanewchemoenzymaticapproachforthesynthesisofperacetylatedlactosamineintermediateforthesynthesisofpharmacologicallyactivecompoundsmonitoredbyrphplcmethod AT alazzamkhaldunmohammad developmentandoptimizationofanewchemoenzymaticapproachforthesynthesisofperacetylatedlactosamineintermediateforthesynthesisofpharmacologicallyactivecompoundsmonitoredbyrphplcmethod AT abudayehzeadhelmi developmentandoptimizationofanewchemoenzymaticapproachforthesynthesisofperacetylatedlactosamineintermediateforthesynthesisofpharmacologicallyactivecompoundsmonitoredbyrphplcmethod AT hassounehloaykhaled developmentandoptimizationofanewchemoenzymaticapproachforthesynthesisofperacetylatedlactosamineintermediateforthesynthesisofpharmacologicallyactivecompoundsmonitoredbyrphplcmethod |