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Fiege K, Lünsdorf H, Atarijabarzadeh S, Mischnick P
Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles
Beilstein Journal of Organic Chemistry 8 (2012)
551-566
Aureobasidium pullulans
(NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Publication DOI: 10.3762/bjoc.8.63Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: p.mischnick

tu-braunschweig.de
Institutions: Institute for Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany, Department of Vaccinology and Applied Microbiology, EM-Unit, Helmholtz Centre for Infection Research, Braunschweig, Germany, Fiber and Polymer Technology, KTH Royal Institute of Technology, Stockholm, Sweden
Cyanoethylglucans with a degree of substitution in the range of 0.74 to 2.40 for dextran and 0.84 to 2.42 for pullulan were obtained by Michael addition of acrylonitrile to the glucans under various conditions. Products were thoroughly characterized, comprising elementary analysis, NMR and ATR-IR spectroscopy, and analysis of the substituent distribution in the glucosyl units by GC-FID and GC-MS of the constituting monosaccharide derivatives. Nanostructuring of the highly substituted cyanoethylpolysaccharides was performed by dialysis against a non-solvent. In the presence of ferromagnetic iron-oxide nanoparticles, multicore cyanoethylglucan- coated ferromagnetic nanoparticles were formed by selective entrapment. The specific interaction between cyano groups and iron could be proven. The size distribution and morphology of the nanoparticles were analyzed by dynamic light scattering (DLS), scanning electron microscopy (SEM) and energy-filtered transmission electron microscopy (EF-TEM) with parallel electron energy loss spectroscopy (PEELS).
cyanoethyldextran, cyanoethylpullulan, ferromagnetic nanoparticles, glycan nanostructures, substitution pattern
Structure type: polymer chemical repeating unit ; 100000
Location inside paper: Fig.1, left top, fig.5(b,d)
Trivial name: pullulan
Compound class: O-polysaccharide, glucan
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420419,IEDB_420420,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
Methods: 1H NMR, GLC-MS, IR, ESI-MS, GLC, SEM, derivatization, elementary analysis, TEM
Comments, role: there are also 1H NMR signals in DMSO
Related record ID(s): 41589, 44495, 44496, 44497, 45035, 45814, 45934, 45961, 46041, 47851, 48389, 48424, 48425, 48441, 48447, 48467, 48468, 48469, 49231, 49289, 49953, 49977, 49978, 49979, 49995, 49999, 50000, 50002, 50007, 50014, 50071, 50081, 50082, 50083, 50111, 50113, 104020
NCBI Taxonomy refs (TaxIDs): 5580Reference(s) to other database(s): GTC:G71532WE
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Expand this record
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Fiege K, Lünsdorf H, Atarijabarzadeh S, Mischnick P
Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles
Beilstein Journal of Organic Chemistry 8 (2012)
551-566
Leuconostoc mesenteroides
(NCBI TaxID 1245,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Publication DOI: 10.3762/bjoc.8.63Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: p.mischnick

tu-braunschweig.de
Institutions: Institute for Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany, Department of Vaccinology and Applied Microbiology, EM-Unit, Helmholtz Centre for Infection Research, Braunschweig, Germany, Fiber and Polymer Technology, KTH Royal Institute of Technology, Stockholm, Sweden
Cyanoethylglucans with a degree of substitution in the range of 0.74 to 2.40 for dextran and 0.84 to 2.42 for pullulan were obtained by Michael addition of acrylonitrile to the glucans under various conditions. Products were thoroughly characterized, comprising elementary analysis, NMR and ATR-IR spectroscopy, and analysis of the substituent distribution in the glucosyl units by GC-FID and GC-MS of the constituting monosaccharide derivatives. Nanostructuring of the highly substituted cyanoethylpolysaccharides was performed by dialysis against a non-solvent. In the presence of ferromagnetic iron-oxide nanoparticles, multicore cyanoethylglucan- coated ferromagnetic nanoparticles were formed by selective entrapment. The specific interaction between cyano groups and iron could be proven. The size distribution and morphology of the nanoparticles were analyzed by dynamic light scattering (DLS), scanning electron microscopy (SEM) and energy-filtered transmission electron microscopy (EF-TEM) with parallel electron energy loss spectroscopy (PEELS).
cyanoethyldextran, cyanoethylpullulan, ferromagnetic nanoparticles, glycan nanostructures, substitution pattern
Structure type: structural motif or average structure ; 6000
Location inside paper: Fig.1, left bottom, fig.4 (b,d)
Trivial name: dextran
Compound class: O-polysaccharide, glucan
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_2346541,IEDB_983931,SB_192
Methods: 1H NMR, GLC-MS, IR, ESI-MS, GLC, SEM, derivatization, elementary analysis, TEM
Comments, role: there are also 1H NMR signals in DMSO
Related record ID(s): 44494, 44496, 44497
NCBI Taxonomy refs (TaxIDs): 1245Reference(s) to other database(s): GTC:G56089RV
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Expand this record
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Fiege K, Lünsdorf H, Atarijabarzadeh S, Mischnick P
Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles
Beilstein Journal of Organic Chemistry 8 (2012)
551-566
|
?%Subst-(1-6)-+
|
?%Subst-(1-2)-+ |
| |
?%Subst-(1-6)-+ | |
| | |
?%Subst-(1-2)-+ | | |
| | | |
?%Subst-(1-4)-+ | | | |
| | | | |
?%Subst-(1-2)-+ | | | | |
| | | | | |
-6)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-
| | |
?%Subst-(1-3)-+ | |
| |
?%Subst-(1-3)-+ |
|
?%Subst-(1-3)-+
Subst = cyanoethanol = SMILES N#CC{1}CO |
Show graphically |
Aureobasidium pullulans
(NCBI TaxID 5580,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.3762/bjoc.8.63Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: p.mischnick

tu-braunschweig.de
Institutions: Institute for Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany, Department of Vaccinology and Applied Microbiology, EM-Unit, Helmholtz Centre for Infection Research, Braunschweig, Germany, Fiber and Polymer Technology, KTH Royal Institute of Technology, Stockholm, Sweden
Cyanoethylglucans with a degree of substitution in the range of 0.74 to 2.40 for dextran and 0.84 to 2.42 for pullulan were obtained by Michael addition of acrylonitrile to the glucans under various conditions. Products were thoroughly characterized, comprising elementary analysis, NMR and ATR-IR spectroscopy, and analysis of the substituent distribution in the glucosyl units by GC-FID and GC-MS of the constituting monosaccharide derivatives. Nanostructuring of the highly substituted cyanoethylpolysaccharides was performed by dialysis against a non-solvent. In the presence of ferromagnetic iron-oxide nanoparticles, multicore cyanoethylglucan- coated ferromagnetic nanoparticles were formed by selective entrapment. The specific interaction between cyano groups and iron could be proven. The size distribution and morphology of the nanoparticles were analyzed by dynamic light scattering (DLS), scanning electron microscopy (SEM) and energy-filtered transmission electron microscopy (EF-TEM) with parallel electron energy loss spectroscopy (PEELS).
cyanoethyldextran, cyanoethylpullulan, ferromagnetic nanoparticles, glycan nanostructures, substitution pattern
Structure type: structural motif or average structure
Location inside paper: Fig.1, right top, fig.5
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420419,IEDB_420420,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
Methods: 1H NMR, GLC-MS, IR, ESI-MS, GLC, SEM, derivatization, elementary analysis, TEM
Comments, role: the cyanoethylation degree is equal 0.84-2.42; there are also 1H NMR signals in DMSO
Related record ID(s): 44494, 44495, 44497
NCBI Taxonomy refs (TaxIDs): 5580
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Fiege K, Lünsdorf H, Atarijabarzadeh S, Mischnick P
Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles
Beilstein Journal of Organic Chemistry 8 (2012)
551-566
|
?%Subst-(1-4)-+
|
/Variants 0/-+ |
| |
-6)-a-D-Glcp-(1-
|
?%Subst-(1-2)-+
/Variants 0/ is:
?%Subst-(1-6)-+
|
?%Subst-(1-3)-+ |
| |
?%Subst-(1-2)-?%a-D-Glcp-(1-3)-
|
?%Subst-(1-4)-+
OR (exclusively)
?%Subst-(1-3)-
Subst = 2-cyanoethanol = SMILES N#CC{1}CO |
Show graphically |
Leuconostoc mesenteroides
(NCBI TaxID 1245,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
The structure was elucidated in this paperPublication DOI: 10.3762/bjoc.8.63Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: p.mischnick

tu-braunschweig.de
Institutions: Institute for Food Chemistry, Technische Universität Braunschweig, Braunschweig, Germany, Department of Vaccinology and Applied Microbiology, EM-Unit, Helmholtz Centre for Infection Research, Braunschweig, Germany, Fiber and Polymer Technology, KTH Royal Institute of Technology, Stockholm, Sweden
Cyanoethylglucans with a degree of substitution in the range of 0.74 to 2.40 for dextran and 0.84 to 2.42 for pullulan were obtained by Michael addition of acrylonitrile to the glucans under various conditions. Products were thoroughly characterized, comprising elementary analysis, NMR and ATR-IR spectroscopy, and analysis of the substituent distribution in the glucosyl units by GC-FID and GC-MS of the constituting monosaccharide derivatives. Nanostructuring of the highly substituted cyanoethylpolysaccharides was performed by dialysis against a non-solvent. In the presence of ferromagnetic iron-oxide nanoparticles, multicore cyanoethylglucan- coated ferromagnetic nanoparticles were formed by selective entrapment. The specific interaction between cyano groups and iron could be proven. The size distribution and morphology of the nanoparticles were analyzed by dynamic light scattering (DLS), scanning electron microscopy (SEM) and energy-filtered transmission electron microscopy (EF-TEM) with parallel electron energy loss spectroscopy (PEELS).
cyanoethyldextran, cyanoethylpullulan, ferromagnetic nanoparticles, glycan nanostructures, substitution pattern
Structure type: structural motif or average structure
Location inside paper: Fig.1, right bottom, fig.4
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_2346541,IEDB_983931,SB_192
Methods: 1H NMR, GLC-MS, IR, ESI-MS, GLC, SEM, derivatization, elementary analysis, TEM
Comments, role: the cyanoethylation degree is equal 0.74-2.40; there are also 1H NMR signals in DMSO
Related record ID(s): 44494, 44495, 44496
NCBI Taxonomy refs (TaxIDs): 1245
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
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