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

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ABUALASSAL QAIS IBRAHIM; MOHAMMAD AL AZZAM KHALDUN; HELMI ABUDAYEH ZEAD; KHALED HASSOUNEH LOAY

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Journal Paper

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Journal: Advanced Pharmaceutical Bulletin Year:2017 | Volume:7 | Issue:2 Page(s): 313-321

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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

Author(s)

ABUALASSAL QAIS IBRAHIM | MOHAMMAD AL AZZAM KHALDUN | HELMI ABUDAYEH ZEAD | KHALED HASSOUNEH LOAY | Issue Writer Certificate

Keywords

GLYCOSYLATION REACTION

CHEMO-ENZYMATIC SYNTHESIS

REGIOSELECTIVITY

HIGH PERFORMANCE LIQUID

CHROMATOGRAPHY

FLASH COLUMN CHROMATOGRAPHY

CANDIDA RUGOSA

Abstract

Purpose: To describe a chemoenzymatic approach joining an enzymatic regioselective hydrolysis of peracetylatedN -acetyl-a-D-glucosamine (A) with a mild controlled acyl relocation which resulted 2-acetamido-2 deoxy-1, 3, 6-tri-O-acetyl-a-D-glucopyranose (1B).Methods: Immobilization of lipase on decaoctyl (DSEOD) and octyl-agarose (OSCL) was carried out as reported by the work of Bastidaet 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 ondecaoctylsepabeads 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 peracetylatedN -acetyl-α-D-glucosamine (A) with a mild monitored acyl movement which led to 2-acetamido-2-deoxy-1, 3, 6-tri-O-acetyl-a-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 1HNMR and mass spectrometry.Conclusion: An efficient chemoenzymatic procedure to optimize the preparation of peracetylated lactosamineB containing acetyl ester as extraordinary protecting group is presented. CompoundB 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.

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References

REGIOSELECTIVE DEPROTECTION OF THE MONOSACCHARIDEBEARING THIOCYANOMETHYL GROUP AT THE ANOMERIC POSITION MONITORED BY REVERSED-PHASE HPLC METHOD

Cite

APA: Copy

ABUALASSAL, QAIS IBRAHIM, MOHAMMAD AL AZZAM, KHALDUN, HELMI ABUDAYEH, ZEAD, & KHALED HASSOUNEH, LOAY. (2017). 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. ADVANCED PHARMACEUTICAL BULLETIN, 7(2), 313-321. SID. https://sid.ir/paper/331874/en

Vancouver: Copy

ABUALASSAL QAIS IBRAHIM, MOHAMMAD AL AZZAM KHALDUN, HELMI ABUDAYEH ZEAD, KHALED HASSOUNEH LOAY. 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. ADVANCED PHARMACEUTICAL BULLETIN[Internet]. 2017;7(2):313-321. Available from: https://sid.ir/paper/331874/en

IEEE: Copy

QAIS IBRAHIM ABUALASSAL, KHALDUN MOHAMMAD AL AZZAM, ZEAD HELMI ABUDAYEH, and LOAY KHALED HASSOUNEH, “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,” ADVANCED PHARMACEUTICAL BULLETIN, vol. 7, no. 2, pp. 313–321, 2017, [Online]. Available: https://sid.ir/paper/331874/en

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