Enzymatic synthesis of cyclodextrins with α-glucosylfluoride as a substrate for cyclodextrin-α(1→4)glucosyltransferase

Treder, Wolfgang; Thiem, Joachim; Schlingmann, M.

doi:10.1016/s0040-4039(00)85277-6

Cited by 32 publications

(7 citation statements)

References 11 publications

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“…In case of N-acetyllactosamine as acceptor 14% of trisaccharides were isolated. The a,2-6 isomer, previously obtained by sialyltrans- [43]. dling, immobilizing treatments and the like which renders them interesting also for larger scale preparations.…”

Section: Glycohydrolases In Glycosylationmentioning

confidence: 99%

“…In case of N-acetyllactosamine as acceptor 14% of trisaccharides were isolated. The a,2-6 isomer, previously obtained by sialyltrans- [43].…”

Section: Glycohydrolases In Glycosylationmentioning

confidence: 99%

“…It could be demonstrated with immobilized CGT that a-D-glucopyranosyl fluoride was accepted as an unnatural substrate to give only a-(30%), /3-(38%) and no y-cyclodextrins, and in addition maltooligomers (32%) (Fig. 15) [43].…”

Section: Glycosylation By Glycosyltransferasesmentioning

confidence: 99%

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Applications of enzymes in synthetic carbohydrate chemistry

Thiem

1995

FEMS Microbiology Reviews

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By photosynthesis 200 billion tons of glucose are formed per annum most of which remains in the sugar state. Thus, the well-known properties of saccharides as the basis for structural materials and energy stores is well established. Increasingly, focus is being addressed to their functions as recognition molecule. Therefore, carbohydrate chemistry became en vogue again as documented by classical syntheses of complex hetero-oligosaccharides employing protecting and activating group chemistry. In recent years enzymatic methods for acylation and deacylation in saccharide chemistry came into use. Novel saccharides could be approached following aldolase-catalyzed de novo syntheses. The very complex task of stereospecific glycosylation was addressed by use of enzymes. With glycohydrolases via transglycosylation as well as with glycosyltransferases including cofactor regenerating circles advances were made. Modified acceptor and also donor substrates allowed access to oligosaccharides in preparative quantities. This paper will discuss these modem developments and will focus on some selected examples from others' and our own laboratory.

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Section: Glycohydrolases In Glycosylationmentioning

confidence: 99%

“…In case of N-acetyllactosamine as acceptor 14% of trisaccharides were isolated. The a,2-6 isomer, previously obtained by sialyltrans- [43].…”

Section: Glycohydrolases In Glycosylationmentioning

confidence: 99%

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Applications of enzymes in synthetic carbohydrate chemistry

Thiem

1995

FEMS Microbiology Reviews

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“…We prepared recombinant human G-EM by expression in Escherichia coli,a sr eportedp reviously. [22] As ap rototypical acceptors ubstrate, we employed af luorescently labeled disaccharide Mana1-2Mana-C 3 H 6 NH-Dansyl (2)i nl ight of our previousG -EMs tudy, [23] with Glca1-3Mana-F (1)a st he glycosyl donor.A si np revious studies, [24][25][26][27][28] the assay was conducted in phosphate buffer (pH 7.0) containing 1, 2 (1/2,1 :4), and recombinant human G-EM (Scheme 1). After 30 min at 37 8C, HPLC analysis of the reaction mixture revealed an ew peak, which was assigneda s3 [23] ( Figure 1A).…”

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confidence: 99%

Endo‐α‐Mannosidase‐Catalyzed Transglycosylation

et al. 2017

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In order for facilitating the synthesis of oligosaccharides, transglycosylation reactions mediated by glycoside hydrolases have been studied in various contexts. In this study, we examined the transglycosylating activity of a Golgi endo-α-mannosidase. We prepared various glycosyl donors and acceptors, and recombinant human Golgi endo-α-mannosidase and its various mutants were expressed. The enzyme was able to mediate transglycosylation from α-glycosyl-fluorides. Systematic screening of various point mutants revealed that the E407D mutant had excellent transglycosylation activity and extremely low hydrolytic activity. Substrate specificity analysis revealed that minimum motif required for glycosyl acceptor is Manα1- 2Man. The synthetic utility of the enzyme was demonstrated by generation of a high-mannose-type undecasaccharide (Glc Man GlcNAc ).

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“…The activating group at the anomeric centre of the donor is either a nucleoside diphosphate in the case of the Leloir transferases or a simple sugar-1-phosphate in the case of the non-Leloir glycosyltransferases. [8][9][10] Examples of enzymes from the non-Leloir glycosyl transferase class are phosphorylases, [11][12][13][14][15][16][17] cyclodextrin glycosyltransferases, [18][19][20] and lipid A synthetase. 21 This report describes syntheses employing a non-Leloir enzyme, the b-1AE3-galactosyl-N-acetylhexosamine phosphorylase from Bifidobacterium bifidum DSM 20082 to give the following Galp-b-(1AE3) derivatives: b-D-…”

mentioning

confidence: 99%