β-Glycosidases: An alternative enzyme based method for synthesis of alkyl-glycosides

Rather, Mohd Younis; Mishra, Saroj

doi:10.1186/2043-7129-1-7

Sustainable Chemical Processes

Table 3 Synthesis of alkyl glycosides by β–glycosidases via transglycosylation route

From: β-Glycosidases: An alternative enzyme based method for synthesis of alkyl-glycosides

Source of enzyme	Glycosyl donor	Glycosyl acceptor	Product	Yield (%)	Time (h)	Reference
Trichoderma reesei β-xylosidase	Methyl-β-D-xyloside	Ethanol, Propanol	Ethyl-β-D-xyloside, Propyl-β-D-xyloside	52-55	12	[5]
Candida molischiana35M5N β- glucosidase	Cellobiose	1-decanol	Decyl-β-D-glucopyranoside	Lower yields	20	[60]
Almond β-glucosidase	Methyl-β-D-glucoside	Hexanol	Hexyl-β-D-glucopyranoside	25	24	[55]
Almond β-glucosidase	Cellobiose			28	48	[55]
β-glucosidase II Aspergillus niger	Cellobiose	Methanol	Methyl-β-D-glucopyranoside	82	0.5	[56]
β-glucosidase II Aspergillus niger		Ethanol	Ethyl-β-D- glucopyranoside	55		[56]
Almond β-glucosidase	Cellobiose	Methanol	Methyl-β-D-glucopyranoside	37	5	[53]
β-glucosidase from Fusarium oxysporum	Cellobiose	Methanol	Methyl-β-D-glucopyranoside	54.4		[57]
	Gentiobiose			51.3
	Amygdalin			63.4
	Arbutin			72.2
	Salicin			58
	pNPG			74.2
Aspergillus niger β-glucosidase II	Cellobiose	Methanol	Methyl-β-D-glucopyranoside	83	6	[58]
Aspergillus niger β-glucosidase II		Ethanol	Ethyl-β-D- glucopyranoside	53	3	[58]
Hyperthermophilic β-glycosidase	Lactose	Heptanol	Heptyl-β-D-glucopyranoside	22.5	25	[61]
β-Glucosidase from Thai Rosewood	pNPG	C1-C4 1° alcohols	β-alkyl glucosides	C1 = 97	7	[62]
				C2 = 93
				C3 = 81
				C4 = 89
β-Galactosidase Penicillium canescencs	Lactose	Heptanol	Heptyl-β-D- galactopyranoside	43	80	[19]
		Octanol	Octyl-β-D- galactopyranoside	45
		Nonanol	Nonyl-β-D- galactopyranoside	37
Almond β- glucosidase	pNPG	Octanol	Octyl-β-D- glucopyranoside	42	NA	[63]
β-glucosidase from C. Saccharolyticum	pNPG	Octanol	Octyl-β-D- glucopyranoside	45	NA	[63]
β-glycosidase from bitter almond	Methyl-β- D-glucoside	Hexanol	Hexyl-β-D- glucopyranoside	21	155	[64]
β-galactosidase from Aspergillus oryzae	Lactose		Hexyl-β-D- galactopyranoside	4		[64]
β-glycosidases from Sulfolobus solfataricus (LacS)/ Pyrococcus furiosus (CelB).	Lactose	Hexanol	Hexyl-β-D- glucopyranoside/Hexyl-β-D- galactopyranoside	29/28	10	[16]
	Lactose	Hexanol	Hexyl-β-D- glucopyranoside/Hexyl-β-D- galactopyranoside	41/63	20	[16]
Almond β- glucosidase adsorbed on Celite R-640®	pNPG	Octanol	Octyl-β-D- glucopyranoside	37.2	650	[17]
Almond β- glucosidase	pNPG	Primary alcohols (C1-C6)	β-alkyl glucosides	C1 = 81	24	[65]
				C2 = 64
				C3 = 48
				C4 = 25
				C5 = 22
				C6 = 18
Whole cells of Bacillus pseudofirmus	Lactose	Hexanol	Hexyl-β-D-galactopyranoside	50	3	[26]
Whole cells of Bacillus pseudofirmus	Lactose	Octanol	Octyl-β-D-galactopyranoside	26	20	[26]
Thermotoga neapolitana β-glucosidase B	pNPG	Hexanol	Hexyl-β-D- glucoside	80.3	3	[66]
β-galactosidase from Aspergillus aculeatus displayed on Yeast cells	pNPG	Hexanol	Hexyl-β-D- glucoside	27.3	12	[27]
β-glucosidase Sclerotinia sclerotium	Cellobiose	Primary alcohols (C4-C8)	β-alkyl- glucosides	Moderate yields	30	[38]
β-galactosidase displayed on Bacillus spores	Lactose	Octanol	Octyl-β-D- galactopyranoside	27.7	24	[29]
Pseudoaltermonas 22b β- galactosidase	Lactose	1° alcohols (C5-C9)	Pentyl-β-D- galactopyranoside	31	48	[68]
			Hexyl-β-D- galactopyranoside	28
			Heptyl- β-D- galactopyranoside	18
			Octyl- β-D- glactopyranoside	9
			Nonoyl- β-D- galactopyranoside	5
β-D-Galactosidase from Paenibacillus thiaminolyticus	pNP-β-D- Fucose	Methanol	Methyl-β-D-fucoside	94	2.5	[59]
		Ethanol	Ethyl-β-D-fucoside	72
		Propanol	Propyl-β-D-fucoside	56 4
		Octanol	Octyl-β-D-fucoside	15 2
β-D-galactosidase from Aspergillus niger	Lactose	Hexanol	Hexyl-β-D-pyranoside	10	3	[69]
β-D-galactosidase from Aspergillus niger	Lactose	Heptanol	Heptyl-β-D-galacto pyranoside	8	3	[69]
Cell bound β-glucosidase of pyranoside Pichia etchellsii	pNPG	Octanol	Octyl-β-D-glucopyranoside	70	4	[20]
β-Galactosidase on cell surface of Bacillus subtilis	Lactose	Octanol	Octyl-β-D-galactopyranoside	33.7	24	[28]
Xylanase from Thermobacillus xylanilyticus	Birchwood xylan	Pentanol	Pentyl-β-D-xylobioside	85	1	[70]
		Octanol	Octyl-β-D-xyloside	8
			Octyl-β-D-xylobioside	14
			Octyl-β-D-xylotrioside	21
Cell bound β-glucosidase of Pichia etchellsii	Methyl-β- D-glucoside	Hexanol	Hexyl-β-D-glucopyranoside	48	6	[24]
		Octanol	Octyl-β-D-glucopyranoside	53
		Decanol	Decyl-β-D-glucopyranoside	27
		Dodecanol	Dodecyl-β-D-glucopyranoside	13

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