Directed enzymatic synthesis of linear and branched glucooligosaccharides, using cyclodextrin-glucanosyltransferase

Vetter, Dirk; Thorn, W.; Brunner, Heiko; König, Wilfried Α.

doi:10.1016/0008-6215(92)80006-m

Cited by 18 publications

(6 citation statements)

References 8 publications

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“…The reported results, however, were unclear because mixtures of branched oligosaccharides terminated by panose were obtained and no experimental conditions were given. In contrast, Vetter et al found that under kinetic control, the elongation reaction occurred only at the 4 II ‐OH of panose 8. Summers and French described a different strategy for the synthesis of this type of branched oligosaccharide by using pullulan and dextran as acceptors 9.…”

Section: Resultsmentioning

confidence: 99%

“…Cyclodextrin glycosyltransferase (CGTase; EC 2.4.1.19, GH family 13) has previously been employed in the preparation of branched gluco ‐oligosaccharides by coupling cyclohexaamylose and panose ( 1 ) 7, 8. The reported results, however, were unclear because mixtures of branched oligosaccharides terminated by panose were obtained and no experimental conditions were given.…”

Section: Resultsmentioning

confidence: 99%

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Chemoenzymatic Synthesis of Branched Oligo‐ and Polysaccharides as Potential Substrates for Starch Active Enzymes

et al. 2003

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Oligo- and polysaccharides embodying the alpha-maltotriosyl-6(II)-maltotetraosyl structure were readily synthesized by transglycosylation of maltosyl fluoride onto panose and pullulan catalysed by the bacterial transglycosylase cyclodextrin glycosyltransferase (CGTase). The two products obtained proved useful for increasing the knowledge of substrate binding and processing at the active site of barley limit dextrinase that is involved in the metabolism of amylopectin by acting upon its branch points.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Chemoenzymatic Synthesis of Branched Oligo‐ and Polysaccharides as Potential Substrates for Starch Active Enzymes

et al. 2003

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“…Starch, CD and MOS can act as substrates in all four reactions. Starch is generally a donor of glucose residues, CD can be recognised as a donor (French et al ., 1954;Vetter et al ., 1992;Kobayashi et al ., 1995), MOS can be recognised as donors as well as acceptors, depending on medium composition, and short oligosaccharides are acceptors. Even if this enzyme shows a high donor structure specificity (linear or cyclic polymers of glucose residues with a(1 0/4) glucosidic bonds), its poor acceptor specificity allows the use of a large range of acceptor molecules (Nakamura et al ., 1994;Bender, 1985) so long as their non reducing end has the C 2 , C 3 , and C 4 configuration of a glucopyranose.…”

Section: Introductionmentioning

confidence: 94%

Purification and Characterisation of Polyglucosyl-fructosides Produced by Means of Cyclodextrin Glucosyl Transferase

Monthieu

Guibert

Taravel

et al. 2003

Biocatalysis and Biotransformation

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The capacity of CGTase for using bCD (beta cyclodextrin) as glucosyl donor and transferring it to sucrose molecules was investigated. We showed that this enzyme was able to produce polyglucosyl-fructosides (G n F) by a coupling reaction between bCD and sucrose. Maltooligosaccharides were also synthesised but in lesser amounts. The degree of polymerisation (DP) of the different products was limited to a value of 8 and this allowed us to purify all of them by size exclusion chromatography. Mass spectrometry and NMR analysis of the unknown products revealed that they consisted of linear maltooligosaccharides of various DP bound to the glucose moiety of a sucrose molecule by a a(10/4) linkage.

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“…It is known that the acceptor can be glucose, a maltooligosaccharide or a derivative thereof with a free 4-hydroxyl group. Acceptors can have either aor b-configuration at C-1, but galacto or manno configuration prevents the substance from acting as acceptor (Vetter et al, 1992). Alkyl glycosides with 1-3 glucose residues and hydrocarbon chains between 10 and 14 carbon atoms long are good acceptor substrates (Svensson et al, 2009).…”

Section: Requirements For An Efficient Coupling Reactionmentioning

confidence: 99%

Efficient synthesis of a long carbohydrate chain alkyl glycoside catalyzed by cyclodextrin glycosyltransferase (CGTase)

Svensson¹,

Ulvenlund²,

Adlercreutz³

2009

Biotech & Bioengineering

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Alkyl glycosides with long carbohydrate groups are surfactants with attractive properties but they are very difficult to synthesize. Here, a method for extension of the carbohydrate group of commercially available dodecyl-beta-d-maltoside (DDM) is presented. DDM was converted to dodecyl-beta-d-maltooctaoside (DDMO) in a single step by using a CGTase as catalyst and alpha-cyclodextrin (alpha-CD) as glycosyl donor. The coupling reaction is under kinetic control and the maximum yield depends on the selectivity of the enzyme. The Bacillus macerans CGTase favored the coupling reaction while the Thermoanaerobacter enzyme also catalyzed disproportionation reactions leading to a broader product range. A high ratio alpha-CD/DDM favored a high yield of DDMO and yields up to 80% were obtained using the B. macerans enzyme as catalyst.

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Directed enzymatic synthesis of linear and branched glucooligosaccharides, using cyclodextrin-glucanosyltransferase

Cited by 18 publications

References 8 publications

Chemoenzymatic Synthesis of Branched Oligo‐ and Polysaccharides as Potential Substrates for Starch Active Enzymes

Chemoenzymatic Synthesis of Branched Oligo‐ and Polysaccharides as Potential Substrates for Starch Active Enzymes

Purification and Characterisation of Polyglucosyl-fructosides Produced by Means of Cyclodextrin Glucosyl Transferase

Efficient synthesis of a long carbohydrate chain alkyl glycoside catalyzed by cyclodextrin glycosyltransferase (CGTase)

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