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1. (Article ID: 7897)
Franken J, Brandt BA, Tai SL, Bauer FF
Biosynthesis of levan, a bacterial extracellular polysaccharide, in the yeast Saccharomyces cerevisiae
PLoS One 8(10) (2013)
e77499 (1-14)
Levans are fructose polymers synthesized by a broad range of micro-organisms and a limited number of plant species as non-structural storage carbohydrates. In microbes, these polymers contribute to the formation of the extracellular polysaccharide (EPS) matrix and play a role in microbial biofilm formation. Levans belong to a larger group of commercially important polymers, referred to as fructans, which are used as a source of prebiotic fibre. For levan, specifically, this market remains untapped, since no viable production strategy has been established. Synthesis of levan is catalysed by a group of enzymes, referred to as levansucrases, using sucrose as substrate. Heterologous expression of levansucrases has been notoriously difficult to achieve in Saccharomyces cerevisiae. As a strategy, this study used an invertase (Δsuc2) null mutant and two separate, engineered, sucrose accumulating yeast strains as hosts for the expression of the levansucrase M1FT, previously cloned from Leuconostoc mesenteroides. Intracellular sucrose accumulation was achieved either by expression of a sucrose synthase (Susy) from potato or the spinach sucrose transporter (SUT). The data indicate that in both Δsuc2 and the sucrose accumulating strains, the M1FT was able to catalyse fructose polymerisation. In the absence of the predicted M1FT secretion signal, intracellular levan accumulation was significantly enhanced for both sucrose accumulation strains, when grown on minimal media. Interestingly, co-expression of M1FT and SUT resulted in hyper-production and extracellular build-up of levan when grown in rich medium containing sucrose. This study presents the first report of levan production in S. cerevisiae and opens potential avenues for the production of levan using this well established industrial microbe. Furthermore, the work provides interesting perspectives when considering the heterologous expression of sugar polymerizing enzymes in yeast.
NCBI PubMed ID: 24147008Publication DOI: 10.1371/journal.pone.0077499Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Bauer FF
sun.ac.za>
Institutions: Institute for Wine Biotechnology, Stellenbosch University, Stellenbosch, Western Cape, South Africa
Methods: 13C NMR, 1H NMR, DNA techniques, TLC, hydrolysis, ethanol precipitation
The publication contains the following compound(s):
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2. (Article ID: 7995)
Rezanka T, Guschina IA
Glycoside esters from lichens of central Asia
Phytochemistry 58(3) (2001)
509-516
Ten compounds isolated from the extract of the central Asian lichens comprised new glycosides and glycoside esters having 18R-hydroxy-dihydroalloprotolichesterinic, 18S-hydroxy-dihydroprotolichesterinic and 18S-hydroxy-neodihydroprotolichesterinic acids, as the aglycones and a saccharide moiety linked at C-18 and also at C-21 made by glucose, xylose or rhamnose. The structures were elucidated using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and ORD) and by biochemical methods.
NMR, MS, glycoside esters, lichens of central Asia, IR, ORD, UV
NCBI PubMed ID: 11557085Publication DOI: 10.1016/S0031-9422(01)00261-8Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: rezanka

biomed.cas.cz
Institutions: Institute of Ecology of the Volga River Basin of the Russian Academy of Sciences, Togliatti, Russia, Institute of Microbiology, Prague, Czech Republic
Methods: 13C NMR, 1H NMR, gel filtration, NMR-2D, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GC, HPLC, UV, extraction, optical rotation measurement, enzymatic assay, HR-FAB-MS, LR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 20076
|
b-D-Glcp-(1-21)-Subst
Subst = 18S-hydroxyneodihydroprotolichesterinic acid = SMILES C{18}[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@H](C)[C@H]1{21}C(=O)O |
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Structure type: monomer
; 533.6797 [M+H]+, 531 [M-H]-
C27H48O10
Compound class: glycoside
- Compound ID: 20077
|
b-D-Glcp-(1-18)-+
|
a-L-Rhap-(1-21)-Subst
Subst = 18R-hydroxydihydroalloprotolichesterinic acid = SMILES C{18}[C@@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@H](C)[C@@H]1{21}C(=O)O |
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Structure type: oligomer
; 679.8234 [M+H]+, 677 [M-H]-
C33H58O14
Compound class: glycoside
- Compound ID: 20080
|
b-D-Glcp-(1-18)-+
|
b-D-Glcp-(1-21)-Subst
Subst = 18S-hydroxyneodihydroprotolichesterinic acid = SMILES C{18}[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@H](C)[C@H]1{21}C(=O)O |
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Structure type: oligomer
; 695.8224 [M+H]+, 693 [M-H]-
C33H58O15
Compound class: glycoside
- Compound ID: 20074
|
a-L-Rhap-(1-21)-Subst
Subst = 18R-hydroxydihydroalloprotolichesterinic acid = SMILES C{18}[C@@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@H](C)[C@@H]1{21}C(=O)O |
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Structure type: monomer
; 517.6801 [M+H]+, 515 [M-H]-
C27H48O9
Compound class: glycoside
- Compound ID: 20079
|
a-L-Rhap-(1-18)-+
|
b-D-Glcp-(1-21)-Subst
Subst = 18S-hydroxyneodihydroprotolichesterinic acid = SMILES C{18}[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@H](C)[C@H]1{21}C(=O)O |
Show graphically |
Structure type: oligomer
; 679.8233 [M+H]+, 677 [M-H]-
C33H58O14
Compound class: glycoside
- Compound ID: 20075
|
b-D-Glcp-(1-21)-Subst
Subst = 18S-hydroxydihydroprotolichesterinic acid = SMILES C{18}[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@@H](C)[C@H]1{21}C(=O)O |
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Structure type: monomer
; 533.6806 [M+H]+, 531 [M-H]-
C27H48O10
Compound class: glycoside
- Compound ID: 20078
|
b-D-Xylp-(1-18)-+
|
b-D-Glcp-(1-21)-Subst
Subst = 18S-hydroxydihydroprotolichesterinic acid = SMILES C{18}[C@H](O)CCCCCCCCCCCCC[C@@H]1OC(=O)[C@@H](C)[C@H]1{21}C(=O)O |
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Structure type: oligomer
; 665.7961 [M+H]+, 663 [M-H]-
C32H56O14
Compound class: glycoside
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3. (Article ID: 10833)
Tomoda M, Gonda R, Ohara N, Shimizu N, Shishido C, Fujiki Y
A glucan having reticuloendothelial system-potentiating and anti-complementary activities from the tuber of Pinellia ternata
Biological and Pharmaceutical Bulletin 17 (1994)
859-861
A glucan, called pinellian G, was isolated from the tuber of Pinellia ternata BREIT. It was homogenous on electrophoresis and gel chromatography, and its molecular mass was estimated to be 1.5 x 10(4). It is composed solely of D-glucose, in addition to a few O-acetyl groups. Methylation analysis, nuclear magnetic resonance and enzymic degradation studies indicated that it is a branched glucan mainly composed of α-1,4-linked D-glucopyranose residues with partially α-1,3-linked units and 4,6-branching points. The glucan showed significant reticuloendothelial system-potentiating activity in a carbon clearance test, as well as pronounced anti-complementary activity.
polysaccharide structure, glucan, immunological activity, Pinellia ternata, pinellian G
NCBI PubMed ID: 7951156Publication DOI: 10.1248/bpb.17.859Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: Kyoritsu College of Pharmacy, Tokyo, Japan
Methods: 13C NMR, gel filtration, GC-MS, TLC, GC, biological assays, HPLC, enzymatic digestion, methylation analysis, hydrolysis, PE
The publication contains the following compound(s):
- Compound ID: 26962
Structure type: homopolymer
; n=3-4
Compound class: maltosaccharide
Reference(s) to other database(s): GTC:G05740LL, CCSD:
45443, CBank-STR:2712
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4. (Article ID: 10858)
Rice KG, Wu P, Brand L, Lee YC
Experimental determination of oligosaccharide three-dimensional structure
Current Opinion in Structural Biology 3 (1993)
669-674
Journal NLM ID: 9107784Publisher: Elsevier
The publication contains the following compound(s):
- Compound ID: 26400
|
a-D-Manp-(1-3)-+ a-L-Fucp-(1-6)-+
| |
b-D-Xylp-(1-2)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-D-GlcNAc
|
a-D-Manp-(1-6)-+ |
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Structure type: oligomer
Compound class: N-glycan
Reference(s) to other database(s): GTC:G36266PV, CCSD:
46364, CBank-STR:16026
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