Synthesis of methyl 5-O-trans-feruloyl-α-l-arabinofuranoside and its use as a substrate to assess feruloyl esterase activity

Enzymatic Synthesis of Hydroxycinnamic Acid Glycerol Esters Using Type A Feruloyl Esterase fromAspergillus niger

“…HAs can be made more water soluble by linking them to hydrophilic compounds such as glycerol and sugars. Although feruloylated sugars can be chemically synthesized, 14,15) in this study we attempted to use enzymatic synthesis because of its higher specificity and the possibility of carrying it out under milder conditions. Feruloyl glycerol was synthesized by transesterification with a lipase from Candida Antarctica, 16) and feruloyl arabinose was synthesized by transesterification with a feruloyl esterase from Sporotrichum thermophile.…”

“…The water solubility of each ester was higher than that of the original acid (Table 2). In the second method, 10 different concentrations (5,10,15,20,25,30,35,40,45, and 50 mg/ml) of each ester were prepared in distilled water. The chemicals were dissolved by boiling for 10 min.…”

A practical high-throughput screening system for feruloyl esterases: Substrate design and evaluation

“…Deacetylation of 4b with 1 M NaOMe in MeOH afforded the expected compound 5b in 77% yield. Selectively acylation of 5b with 4-O-acetylferuloyl chloride [22] under mild basic conditions [8] and subsequent De-O-acetylation with pyrrolidine in dichloromethane [12] gave 2-chloro-4-nitrophenyl 5-O-feruloyl-␣-l-arabinofuranoside 2b (Fig. 1B) in 50% yield.…”

“…However, they always have specificity on monomeric ferulate moiety and are active on its synthetic substrate analogues. The assay of FAEs' activity commonly depends on HPLC, using enzymatic hydrolysis of a variety of natural and synthetic compounds, such as hydroxycinnamic esterified polysaccharide, methyl feulate and their analogues [6][7][8][9]. Recently, several chlorogenic substrates of FAEs have been reported for quantitative assays, such as 4-nitrophenyl ferulate [10,11] (Fig.…”

Chromogenic substrates for feruloyl esterases

“…In practice, enzymatic assay of FAEs has been carried out using commercially available methyl and ethyl esters of hydroxycinnamic acids or using naturally feruloylated oligosaccharides isolated by controlled enzymatic digestion of arabinoxylan. 4 In the same context, Hatfield et al 5 synthesized methyl 5-O-trans-feruloyl-a-L L-arabinofuranoside (FA Ara). In these examples ultraviolet spectrometric measurement was used to detect FAE activity since ferulic acid has a maximum absorption at 340 nm (pH 11) distinct from its esters at 375 nm.…”