Enzymatic synthesis of Acarviosyl-maltooligosaccharides using disproportionating enzyme 1 (original) (raw)
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Two-step enzymatic synthesis of maltooligosaccharide esters
Carbohydrate Research, 2000
Glucose and maltose esters were synthesised in organic media by employing a lipase (E.C. 3.1.1.3) from Candida antarctica. In a second reaction step, a transglycosylation catalysed by a cyclodextrin glycosyltransferase (E.C. 2.4.1.19) from either Paenibacillus sp. F8 or Bacillus sp. strain no. 169 (DSM 2518) extended the degree of polymerisation (DP) of the carbohydrate moieties of the carbohydrate esters. The donor substrates used were either a cyclodextrin, a maltooligosaccharide or starch. The highest rate of low DP maltooligosaccharide ester formation was obtained when starch was used as glycosyl donor and caproyl maltose as glycosyl acceptor. The structures of two of the products were identified by 1 H and 13 C NMR and MALDI-TOF MS as capronate monoesters of maltotriose and maltotetraose, with the ester bond at C-6 of the second glucose unit from the reducing end.
ARKIVOC: archive for organic chemistry
Recently, we have designed chemical strategies leading to C-6 perfunctionalized linear maltoheptaose derivatives via the acetolysis of persubstituted β-cyclodextrin (β-CD) at the 6-positions. This approach has now been extended to the synthesis of monofunctionalized maltoheptaose derivatives. This report deals with the regioselectivity of the ring opening of monosubstituted β-CD and the use of electrospray ionization tandem mass spectrometry (ESI-MS/MS) to identify the substituted unit. In order to confirm our results, a controlled enzymatic degradation of the resulting derivatives, using the glucoamylase of Aspergillus niger, was performed and monitored by liquid chromatography / electrospray ionization mass spectrometry (LC/ESI-MS).
Process Biochemistry, 2007
The transglycosylation activity of a novel -glucosidase from the basidiomycetous yeast 2 Xanthophyllomyces dendrorhous (formerly Phaffia rhodozyma) was studied using maltose as 3 glucosyl donor. The enzyme synthesized oligosaccharides with -(12), -(14) and -4 (16) bonds. Using 200 g/l maltose, the yield of oligosaccharides was 53.8 g/l, with prebiotic 5 oligosaccharides containing at least one -(16) linkage (panose, 6-O--glucosyl-maltotriose 6 and 6-O--isomaltosyl-maltose) being the major products (47.1 g/l). The transglycosylatying 7 yield was 3.6 times higher than the observed with the -glucosidase from Saccharomyces 8 cerevisiae (53.8 vs. 14.7 g/l). Moreover, when increasing the maltose concentration up to 525 9 g/l, the maximum production of tri-and tetrasaccharides reached 167.1 g/l, without altering 10 the percentage of oligosaccharides in the mixture. Compared with other microbial -11 glucosidases in which the main transglycosylation product is a disaccharide, the enzyme from 12 X. dendrorhous yields a final product enriched in trisaccharides and tetrasaccharides. 13 14 15
Tetrahedron, 2000
AbstractÐThe enzymatic acylation of several di-and trisaccharides with acyl donors ranging from 8 to 18 carbon atoms was carried out by transesteri®cation with the corresponding vinyl esters. The reaction was performed in 2-methyl-2-butanol/dimethylsulfoxide mixtures using the lipase from Humicola lanuginosa (immobilized on Celite). Maltose, maltotriose and n-dodecyl maltosides were speci®cally acylated in the primary hydroxyl of the non-reducing-end glucose moiety; the acylation of leucrose occurred preferentially in the primary hydroxyl of the glucose ring. q
Carbohydrate Research, 1994
A convenient one-step synthesis of 2-deoxya-o-arabirw-hexopyranosyl phosphate on a millimolar scale is described by reaction of potato phosphozylase with o-glucal at equimolar phosphate concentration. Furthermore, in the presence of catalytic amounts of phosphate, a Zdeoxy-maltooligosaccharide is obtained from maltotetraose and D-glucal. The water-insoluble oligosaccharide was isolated and characterized by 'H and 13C NMR spectroscopy. An average dp of 20 was thus determined.
Carbohydrate Research, 1999
In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of b-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl b-maltoheptaoside (G 7 -CNP), which was synthesised from b-cyclodextrin (b-CD) using a very convenient chemical method [E. Farkas, L. Jánossy, J. Harangi, L. Kandra, A. Lipták, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3 -6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G 7 -CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G 7 -CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30°C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10°C for 10 min resulted in 89% conversion and G 4 -, G 5 -, and G 6 -CNP oligomers were detected in the ratio of 29:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G 3 6 -CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70 -75%.
Carbohydrate Research, 2001
The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4%-OH group or by reversing its configuration, is reported. For synthesis of the 4%-O-acetylated analog, b-maltose was converted into its per-O-benzylated-4%,6%-O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6%. Acetylation at C-4% of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra-O-benzyl-a/b-D-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-triO -benzyl-1-thio-b-D-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog.