Enzymically Produced Cyclic α‐1,3‐Linked and α‐1,6‐Linked Oligosaccharides of <scp>d</scp>‐Glucose

Côté, Gregory L.; Biely, Peter

doi:10.1111/j.1432-1033.1994.tb20091.x

Cited by 81 publications

(10 citation statements)

References 38 publications

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“…16) Furthermore, it was found that there is CTS in the reaction mixture containing purified enzyme and alternan. 12) This is the first report relating to the enzymatic synthesis of CTS. Later they examined the substrate specificity of alternanase and reported that CTS was also produced from panose by the enzyme.…”

Section: )mentioning

confidence: 96%

“…Cyclic tetrasaccharide (CTS; cyclo{ 6) D Glup (1 3) D Glucp (1 6) D Glucp (1 3) D Glup (1 }) is also one of the nonreducing glucooligosaccharides. 12) A system of synthesizing this cyclic oligosaccharide from starch was recently found in Bacillus globisporus C11. A CTS synthesizing mechanism controlled by two enzymes and the sequence of the genes encoding them were reported in succession.…”

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confidence: 99%

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Production of Cyclic Tetrasaccharide with 6-.ALPHA.-Glucosyltransferase and .ALPHA.-Isomaltosyltransferase

Nishimoto¹,

Aga²,

Kubota³

et al. 2004

J. Appl. Glycosci.

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When saccharides are produced as foodstuffs in fairly large quantities, starch is a very fascinating source. Maltooligosaccharides such as glucose, maltose and maltotetraose are produced by hydrolysis of starch. Cyclodextrins (cyclic oligosaccharides composed of 6, 7, or 8 D glucosyl residues linked by 1,4 linkages ) , 1) isomalto oligosaccharides 2) and nigero oligosaccharides 3) are also produced from starch by enzymatic transfer reactions. In additions, these saccharides can be converted into branched cyclodextrins, sorbitol and maltiotol chemically or enzymically. Starch is used as donor substrate to produce various glycosides such as glucosyl ascorbic acid, 4) and as a source for the production of many saccharide related products. The reason seems to be that not only starch is inexpensive but also various starch related enzymes are present in nature. Indeed, there are many oligosaccharides synthesized enzymically. However, nonreducing glucooligosaccharides synthesized from starch are very few in kind. Examples of such oligosaccharides are trehalose 5 11) and cyclodextrins. Cyclic tetrasaccharide (CTS; cyclo{ 6) D Glup (1 3) D Glucp (1 6) D Glucp (1 3) D Glup (1 }) is also one of the nonreducing glucooligosaccharides.12) A system of synthesizing this cyclic oligosaccharide from starch was recently found in Bacillus globisporus C11. A CTS synthesizing mechanism controlled by two enzymes and the sequence of the genes encoding them were reported in succession. 13,14) These studies indicate that there is a good possibility of industrial production of CTS and a gene cluster related to the synthesis and transport of CTS is present in microorganisms. In this paper, we describe the current study of CTS by focusing on the synthesizing system of CTS from starch.Isolation of CTS-producing bacteria and the producing system in B. globisporus C11. 13)Among some 3000 bacterial strains, strain C11 was isolated from soil from Okayama, Japan, by screening for bacteria producing nonreducing oligosaccharides. Morphological, culture, and physiological characterizations according to Bergey's Manual of Systematic Bacteriology classified strain C11 as a strain of Bacillus globisporus. A nonreducing oligosaccharide was purified from a reaction mixture containing Pinedex #100 (partial hydrolyzate of starch, 1.3% hydrolysis) and the supernatant from B. globisporus C11. This saccharide was found to be identical While searching for nonreducing oligosaccharides that can be produced from α-1,4-glucan as the substrate, we screened bacteria isolated from soil in our own way, and obtained Bacillus globisporus C11, which produces CTS from starch. Two kinds of glycosyltransferase, 6-α-glucosyltransferase (6GT) and α-isomaltosyltransferase (IMT), were purified from the culture supernatant of this strain. It was found that CTS is produced by the sequential action of both enzymes. The genes for IMT (CtsY) and 6GT (CtsZ) were linked together on the chromosome, forming ctsYZ . Both of the gene products showed similarities to α-glucosidases belon...

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Section: )mentioning

confidence: 96%

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confidence: 99%

Production of Cyclic Tetrasaccharide with 6-.ALPHA.-Glucosyltransferase and .ALPHA.-Isomaltosyltransferase

Nishimoto¹,

Aga²,

Kubota³

et al. 2004

J. Appl. Glycosci.

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“…4,5) CTS is smaller than the other cyclic glucans mentioned above and has heterogeneous linkages in its structure. Crystal structure analysis showed that CTS is shaped like a plate with a depression on one side, but does not possess a cavity space like cyclodextrins do.…”

Section: Cloning and Sequencing Of The Genes Encoding Cyclicmentioning

confidence: 97%

Cloning and Sequencing of the Genes Encoding Cyclic Tetrasaccharide-synthesizing Enzymes fromBacillus globisporusC11

Aga

Maruta

Yamamoto

et al. 2002

Bioscience, Biotechnology, and Biochemistry

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The genes for isomaltosyltransferase (CtsY) and 6-glucosyltransferase (CtsZ), involved in synthesis of a cyclic tetrasaccharide from alpha-glucan, have been cloned from the genome of Bacillus globisporus C11. The amino-acid sequence deduced from the ctsY gene is composed of 1093 residues having a signal sequence of 29 residues in its N-terminus. The ctsZ gene encodes a protein consisting of 1284 residues with a signal sequence of 35 residues. Both of the gene products show similarities to alpha-glucosidases belonging to glycoside hydrolase family 31 and conserve two aspartic acids corresponding to the putative catalytic residues of these enzymes. The two genes are linked together, forming ctsYZ. The DNA sequence of 16,515 bp analyzed in this study contains four open reading frames (ORFs) upstream of ctsYZ and one ORF downstream. The first six ORFs, including ctsYZ, form a gene cluster, ctsUVWXYZ. The amino-acid sequences deduced from ctsUV are similar in to a sequence permease and a sugar-binding protein for the sugar transport system from Thermococcus sp. B1001. The third ctsW encodes a protein similar to CtsY, suggested to be another isomaltosyltransferase preferring panose to high-molecular-mass substrates.

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“…In the present study, we employed a new class of cyclic tetrasaccharide (Scheme ), cyclo ‐{→6)‐α‐ d ‐Glc p ‐(1→3)‐α‐ d ‐Glc p ‐(1→6)‐α‐ d ‐Glc p ‐(1→3)‐α‐ d ‐Glc p ‐(1→} or cyclic nigerosyl‐(1→6)‐nigerose (CNN), as a chiral source. CNN was enzymatically produced from starch relatively recently, and so far, only the production, purification, and degradation behaviors have been investigated intensively .…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Photochirogenesis with Novel Cyclic Tetrasaccharide: Enantiodifferentiating Photoisomerization of (Z)‐Cyclooctene with Cyclic Nigerosylnigerose‐Based Sensitizers

et al. 2012

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Isophthalic and terephthalic acid monoesters of cyclic nigerosyl-(1→6)-nigerose (CNN), a cyclic tetrasaccharide composed of four d-glucopyranosyl residues connected by alternating α-1,3- and α-1,6-linkages, were synthesized as novel chiral supramolecular sensitizers for enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to planar chiral (E)-isomer (1E). Despite the saucer-shaped shallow cavity of CNN that does not immediately guarantee strong ground-state interactions with 1Z, the sensitizer-appended CNNs afforded optically active 1E in such enantiomeric excesses that are much improved than those obtained with an α-cyclodextrin analog and comparable with those obtained with a β-cyclodextrin analog. Interestingly, the enantiomeric excess values obtained were a critical function of temperature and solvent to show an inversion of the product chirality by changing the environmental variants. Nevertheless, all of the differential activation parameters calculated from the temperature-dependent enantiomeric excesses gave an excellent compensatory enthalpy-entropy relationship, indicating an operation of a single enantiodifferentiating mechanism in the present chiral photosensitization with modified CNNs.

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Enzymically Produced Cyclic α‐1,3‐Linked and α‐1,6‐Linked Oligosaccharides of d‐Glucose

Cited by 81 publications

References 38 publications

Production of Cyclic Tetrasaccharide with 6-.ALPHA.-Glucosyltransferase and .ALPHA.-Isomaltosyltransferase

Production of Cyclic Tetrasaccharide with 6-.ALPHA.-Glucosyltransferase and .ALPHA.-Isomaltosyltransferase

Cloning and Sequencing of the Genes Encoding Cyclic Tetrasaccharide-synthesizing Enzymes fromBacillus globisporusC11

Supramolecular Photochirogenesis with Novel Cyclic Tetrasaccharide: Enantiodifferentiating Photoisomerization of (Z)‐Cyclooctene with Cyclic Nigerosylnigerose‐Based Sensitizers

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