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KMID : 1094720160210030389
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Biotechnology and Bioprocess Engineering
2016 Volume.21 No. 3 p.389 ~ p.401
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Enzymatic synthesis of propyl-α-glycosides and their application as emulsifying and antibacterial agents
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Charoensapyanan Rittichai
Ito Kazuo
Rudeekulthamrong Prakarn
Kaulpiboon Jarunee
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Abstract
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Alkyl glycosides have been effectively used in many industries because of their biodegradable, emulsification and antibacterial properties. In this study, the alkyl glycoside of propyl glycosides (PGn) was synthesized using β-cyclodextrin (β-CD) and 1-propanol through the transglycosylation reaction of recombinant cyclodextrin glycosyltransferase (CGTase) from the Bacillus circulans A11. The optimal condition for the synthesis of propyl glycosides consisted of an incubation of 1.5% (w/v) β-CD and 500 U/mL of CGTase in a water/propanol content containing 10% (v/v) 1-propanol at pH 6.0, 50°C for 96 h. Upon analysis of the product at the optimal condition by TLC, at least three products which move faster than glucose were observed. These transferred products were formed with molecular weights of 222.1, 384.1 and 546.4 daltons as determined by mass spectrometry analysis; these values were in accordance with propyl glucoside (PG1), propyl maltoside (PG2) and propyl maltotrioside (PG3), respectively. PG1 and PG2 were produced and prepared on a large scale and subsequently purified by preparative TLC. The combined 1H- and 13C-NMR analysis confirmed that the structures of PG1 and PG2 were propyl-α-D-glucopyranoside and propyl-α-D-maltopyranoside, respectively. Both PG1 and PG2 showed emulsification activity and stability in their formation in water and n-hexadecane. Furthermore, the antibacterial activity of both products was determined and it was found that PG2 had a higher antibacterial activity against Staphylococcus aureus and Escherichia coli than that of PG1.
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KEYWORD
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antibacterial activity, cyclodextrin glycosyl-transferase, intermolecular transglycosylation, non-ionic surfactant, propyl glycosides
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