Sporotrichum thermophile type C feruloyl esterase (StFaeC): purification, characterization, and its use for phenolic acid (sugar) ester synthesis

Topakas, Evangelos; Vafiadi, Christina; Stamatis, Haralambos; Christakopoulos, Paul

doi:10.1016/j.enzmictec.2004.12.020

Cited by 82 publications

(64 citation statements)

References 48 publications

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“…However, the fragment at m/z 409 is predicted to be formed after ring cleavage of the oligosaccharide having ferulic acid esterified on the O-2 or O-3 position of the non-reducing L-arabinofuranose ring, exhibiting signal intensity higher than the signal of the O-5 fragment at m/z 463. To the best of the author's knowledge, the enzymatic esterification of the secondary alcohol group of sugars is not possible due to steric hindrance [5,6], therefore this esterified product is hardly or not at all present in the reaction medium.…”

Section: Esi-ms N Analysis Of Feruloylated Productsmentioning

confidence: 99%

“…Various hydroxycinnamic acids (ferulic, p-coumaric, caffeic, sinapic) have widespread industrial potential by virtue of their antioxidant and antimicrobial properties [2,3]. Apart from their use as model substrates for characterisation of FAEs', methyl esters of hydroxycinnamic acids have been recently used as acid donors in transesterification reactions with aliphatic alcohols and carbohydrates [4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

“…FAEs have been used in the synthesis of sugar ferulates such as 5-O-(trans-feruloyl)-L-arabinofuranose [5] [6]. More specifically, StFaeC catalyzed the transfer of the feruloyl group to L-arabinose and L-arabinobiose in a ternary water-organic mixture consisting of n-hexane, t-butanol and water, with about 40% and 20% conversion of sugar to the feruloylated derivative, respectively [7,6].…”

Section: Introductionmentioning

confidence: 99%

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Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

et al. 2007

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Section: Esi-ms N Analysis Of Feruloylated Productsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

et al. 2007

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“…Enzymatic esterification and transesterification of sugars and fatty acids using lipase 18) and feruloyl esterase 19,20) have been reported. The acylation by lipase is regioselective for the primary hydroxyl groups of sugars.…”

Section: Production Of Benzoyl Glucoses By the Reaction Of Sucrose Phmentioning

confidence: 99%

Novel Transglucosylating Reaction of Sucrose Phosphorylase to Carboxylic Compounds

Sugimoto¹,

Nomura²,

Nishiura³

et al. 2008

J. Appl. Glycosci.

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Glycosylation is an important method in the structural modification of bioactive compounds. It is well known that several properties of many active compounds, such as water solubility, 1) taste 2) and stability, 3) are improved by glycosylation. We expect that glycosylation makes active compounds more useful for industrial applications and makes them more effective. In our previous studies, we synthesized arbutin α glycosides by transglycosylation of a cyclomaltodextrin glucanotransferase, and compared the inhibitory activities of arbutin and arbutin α glycosides on human tyrosinase, which is a key enzyme involved in melanin synthesis.4) The inhibitory activity of arbutin on the tyrosinase became much higher with further glycosylation.Enzymatic glycosylation is thought to be more useful method to obtain glycosides than chemical synthesis because it is a one step and strictly stereospecific reaction under mild conditions. Glycosylation using transglucosylation reactions of carbohydrate active enzymes has been reported by many researchers. In those studies, they reported only the reaction to aglycones having glycosyl residues, alcoholic OH groups and phenolic OH groups. There has been no report on transglycosylation reaction to carboxylic groups in various aglycones. Many types of biologically active compounds are used in food and cosmetic materials, and many of these compounds include carboxylic groups in their structures.8,9) Some of these compounds have a strong smell, acidity or low solubility. Therefore, it is important to improve these characteristics to enhance their usefulness for industrial applications.We described here the novel transglycosylation reaction of sucrose phosphorylase on carboxylic compounds. The determined structure of acyl glucoses produced by the enzyme reaction and subsequent non enzymatic reaction and an application study for improvement of the properties of the carboxylic compounds are also highlighted.Transglycosylation reaction of sucrose phosphorylases using sucrose and benzoic acid as substrates. We screened several carbohydrate active enzymes for glycosylation of carboxylic compounds and found that sucrose phosphorylase (EC 2.4.1.7) catalyzes the reaction. 10)Sucrose phosphorylase from S. mutans was incubated with sucrose and benzoic acid at pH 4.2 for 16 h. The incubated mixture was analyzed by HPLC and TLC. In the Abstract: We screened for the carbohydrate-active enzymes that catalyze transglycosylation reactions on carboxylic compounds. Sucrose phosphorylase from Streptococcus mutans showed remarkable transglucosylating activity on benzoic acid, especially under acidic conditions. Sucrose phosphorylase from Leuconostoc mesenteroides also showed the activity, although it was very weak. Three main products were detected from the reaction mixture with sucrose, benzoic acid and S. mutans sucrose phosphorylase. These compounds were identi-

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“…In bio-energy, FAEs could increase the yield of fermentable sugars such as glucose and xylose (Tabka et al, 2006). In biological synthesis, FAEs could be used to convert liposoluble compounds to water-soluble substances (Topakas et al, 2005). FAEs also provide an effective and efficient way to produce ferulic acid, which exhibits broad antioxidant, antimicrobial, anti-inflammatory, antithrombosis and anticancer properties (Koseki, Fushinobu et al, 2009;Mathew & Abraham, 2004).…”

Section: Introductionmentioning

confidence: 99%

Crystallization and preliminary X-ray analysis of a novel halotolerant feruloyl esterase identified from a soil metagenomic library

et al. 2012

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Feruloyl esterase cleaves the ester linkage formed between ferulic acid and polysaccharides in plant cell walls and thus has wide potential industrial applications. A novel feruloyl esterase (EstF27) identified from a soil metagenomic library was crystallized and a complete data set was collected from a single cooled crystal using an in-house X-ray source. The crystal diffracted to 2.9 Å resolution and belonged to space group P2 1 2 1 2 1 , with unitcell parameters a = 94.35, b = 106.19, c = 188.51 Å , = = = 90.00 . A Matthews coefficient of 2.55 Å 3 Da À1 , with a corresponding solvent content of 51.84%, suggested the presence of ten protein subunits in the asymmetric unit.

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Sporotrichum thermophile type C feruloyl esterase (StFaeC): purification, characterization, and its use for phenolic acid (sugar) ester synthesis

Cited by 82 publications

References 48 publications

Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

Structural Characterisation by ESI-MS of Feruloylated Arabino-oligosaccharides Synthesised by Chemoenzymatic Esterification

Novel Transglucosylating Reaction of Sucrose Phosphorylase to Carboxylic Compounds

Crystallization and preliminary X-ray analysis of a novel halotolerant feruloyl esterase identified from a soil metagenomic library

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