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Macko V, Acklin W, Hildenbrand C, Weibel F, Arigoni D
Structure of three isomeric host-specific toxins from Helminthosporium sacchari
Experientia 39(4) (1983)
343-440
|
b-D-Galf-(1-5)-b-D-Galf-(1-2)-+
|
b-D-Galf-(1-5)-b-D-Galf-(1-13)-Subst
Subst = HS-toxin A aglycon = SMILES O{13}[C@H]1CC(C)=C(C[C@@H](C({2}CO)=C)CC2)C2(C)C1 |
Show graphically |
Helminthosporium sacchari
(previously named: Bipolaris sacchari, Drechslera sacchari)
(NCBI TaxID 48696,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/BF01963114Journal NLM ID: 0376547Publisher: Basel, Switzerland: Birkhäuser Verlag
Institutions: Boyce Thompson Institute for Plant Research at Cornell University, Ithaca, USA, Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, Zürich, Switzerland
Extended spectroscopic analysis has led to the derivation of complete structures for the 3 isomeric host-specific toxins C39H64O22 previously isolated from H. sacchari; these compounds represent bis-5-O-(β-galactofuranosyl)-β-galactofuranosides differing in the position of 1 double bond in their sesquiterpenoid aglycone component.
spectroscopic analysis, double bond, complete structure sesquiterpenoid
Structure type: oligomer ; 907 [M+Na]
C
39H
64O
22Location inside paper: Fig. 1, Toxin A, tables 1,2,3
Compound class: glycoside
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606,IEDB_885812
Methods: 13C NMR, 1H NMR, FAB-MS, extraction, CI/D-MS
Comments, role: although sugar 13C NMR referencing was reported as DSS at 0, CSDB staff suggested it was an error in Table 3 footnote, while the reference was 1,4-dioxane at 67.4
Related record ID(s): 44537, 44538
NCBI Taxonomy refs (TaxIDs): 48696
Show glycosyltransferases
NMR conditions: in D2O / (C)
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
2,5 bDGalf 108.0 82.0 77.4 83.7 71.4 63.7
2 bDGalf 106.2-106.9 82.0 77.0 82.5 76.8 62.0
13,5 bDGalf 108.0 82.0 77.4 83.7 71.4 63.7
13 bDGalf 106.2-106.9 82.0 77.0 82.5 76.8 62.0
Subst 46.8 72.4 39.2 123.0 134.6 23.7 37.1 28.3 37.7 36.9 149.0 114.3 71.2 25.4 19.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12
2,5 bDGalf
2 bDGalf
13,5 bDGalf
13 bDGalf
Subst 1.40-1.80 - 2.04-2.40 - 2.24-2.73 2.61 1.64-2.00 1.37 5.11-5.20 4.03-4.23 1.70 1.15
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12
2,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
2 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 |
|---|
| 2,5 | bDGalf | |
| 2 | bDGalf | |
| 13,5 | bDGalf | |
| 13 | bDGalf | |
| | Subst | 1.40
1.80 |
| 2.04
2.40 |
| 2.24
2.73 | 2.61 | 1.64
2.00 | 1.37 | 5.11
5.20 | 4.03
4.23 | 1.70 | 1.15 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 2,5 | bDGalf | 108.0 | 82.0 | 77.4 | 83.7 | 71.4 | 63.7 | |
| 2 | bDGalf | 106.2
106.9 | 82.0 | 77.0 | 82.5 | 76.8 | 62.0 | |
| 13,5 | bDGalf | 108.0 | 82.0 | 77.4 | 83.7 | 71.4 | 63.7 | |
| 13 | bDGalf | 106.2
106.9 | 82.0 | 77.0 | 82.5 | 76.8 | 62.0 | |
| | Subst | 46.8 | 72.4 | 39.2 | 123.0 | 134.6 | 23.7 | 37.1 | 28.3 | 37.7 | 36.9 | 149.0 | 114.3 | 71.2 | 25.4 | 19.3 |
|
There is only one chemically distinct structure:
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Macko V, Acklin W, Hildenbrand C, Weibel F, Arigoni D
Structure of three isomeric host-specific toxins from Helminthosporium sacchari
Experientia 39(4) (1983)
343-440
|
b-D-Galf-(1-5)-b-D-Galf-(1-2)-+
|
b-D-Galf-(1-5)-b-D-Galf-(1-13)-Subst
Subst = HS-toxin B aglycon = SMILES O{13}[C@H]1CC([C@@](C[C@@H](C({2}CO)=C)CC2)([H])C2(C)C1)=C |
Show graphically |
Helminthosporium sacchari
(previously named: Bipolaris sacchari, Drechslera sacchari)
(NCBI TaxID 48696,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/BF01963114Journal NLM ID: 0376547Publisher: Basel, Switzerland: Birkhäuser Verlag
Institutions: Boyce Thompson Institute for Plant Research at Cornell University, Ithaca, USA, Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, Zürich, Switzerland
Extended spectroscopic analysis has led to the derivation of complete structures for the 3 isomeric host-specific toxins C39H64O22 previously isolated from H. sacchari; these compounds represent bis-5-O-(β-galactofuranosyl)-β-galactofuranosides differing in the position of 1 double bond in their sesquiterpenoid aglycone component.
spectroscopic analysis, double bond, complete structure sesquiterpenoid
Structure type: oligomer ; 907 [M+Na]
C
39H
64O
22Location inside paper: Fig. 2, Toxin B, tables 1,2,3
Compound class: glycoside
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606,IEDB_885812
Methods: 13C NMR, 1H NMR, FAB-MS, extraction, CI/D-MS
Synthetic data: biosynthesis
Comments, role: NMR temperature was not specified; although sugar 13C NMR referencing was reported as DSS at 0, CSDB staff suggested it was an error in Table 3 footnote, while the reference was 1,4-dioxane at 67.4
Related record ID(s): 44536, 44538
NCBI Taxonomy refs (TaxIDs): 48696
Show glycosyltransferases
NMR conditions: in D2O / (C)
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
2,5 bDGalf 107.9 82.0 77.3-77.4 83.6 71.3 63.6-63.7
2 bDGalf 106.1-107.2 82.0 77.0-77.3 82.0-82.4 76.7-76.9 62.0
13,5 bDGalf 107.9 82.0 77.3-77.4 83.6 71.3 63.6-63.7
13 bDGalf 106.1-107.2 82.0 77.0-77.3 82.0-82.4 76.7-76.9 62.0
Subst 49.0 75.4 43.0 147.5 44.0 22.7 35.8 25.7 36.5 36.0 149.3 114.9 71.5 108.6 16.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12
2,5 bDGalf
2 bDGalf
13,5 bDGalf
13 bDGalf
Subst 1.28-1.80 3.88 1.97-2.77 1.92 1.63-1.8 2.62 1.8 1.32-1.43 5.19-5.30 4.07-4.22 4.64-4.95 0.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12
2,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
2 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 |
|---|
| 2,5 | bDGalf | |
| 2 | bDGalf | |
| 13,5 | bDGalf | |
| 13 | bDGalf | |
| | Subst | 1.28
1.80 | 3.88 | 1.97
2.77 | 1.92 | 1.63
1.8 | 2.62 | 1.8 | 1.32
1.43 | 5.19
5.30 | 4.07
4.22 | 4.64
4.95 | 0.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 2,5 | bDGalf | 107.9 | 82.0 | 77.3
77.4 | 83.6 | 71.3 | 63.6
63.7 | |
| 2 | bDGalf | 106.1
107.2 | 82.0 | 77.0
77.3 | 82.0
82.4 | 76.7
76.9 | 62.0 | |
| 13,5 | bDGalf | 107.9 | 82.0 | 77.3
77.4 | 83.6 | 71.3 | 63.6
63.7 | |
| 13 | bDGalf | 106.1
107.2 | 82.0 | 77.0
77.3 | 82.0
82.4 | 76.7
76.9 | 62.0 | |
| | Subst | 49.0 | 75.4 | 43.0 | 147.5 | 44.0 | 22.7 | 35.8 | 25.7 | 36.5 | 36.0 | 149.3 | 114.9 | 71.5 | 108.6 | 16.9 |
|
There is only one chemically distinct structure:
Expand this record
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Macko V, Acklin W, Hildenbrand C, Weibel F, Arigoni D
Structure of three isomeric host-specific toxins from Helminthosporium sacchari
Experientia 39(4) (1983)
343-440
|
b-D-Galf-(1-5)-b-D-Galf-(1-2)-+
|
b-D-Galf-(1-5)-b-D-Galf-(1-13)-Subst
Subst = HS-toxin C aglycon = SMILES O{13}[C@H]1C=C(C)[C@@](C[C@@H](C({2}CO)=C)CC2)([H])C2(C)C1 |
Show graphically |
Helminthosporium sacchari
(previously named: Bipolaris sacchari, Drechslera sacchari)
(NCBI TaxID 48696,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperPublication DOI: 10.1007/BF01963114Journal NLM ID: 0376547Publisher: Basel, Switzerland: Birkhäuser Verlag
Institutions: Boyce Thompson Institute for Plant Research at Cornell University, Ithaca, USA, Laboratorium für Organische Chemie, Eidgenössische Technische Hochschule Zürich, Zürich, Switzerland
Extended spectroscopic analysis has led to the derivation of complete structures for the 3 isomeric host-specific toxins C39H64O22 previously isolated from H. sacchari; these compounds represent bis-5-O-(β-galactofuranosyl)-β-galactofuranosides differing in the position of 1 double bond in their sesquiterpenoid aglycone component.
spectroscopic analysis, double bond, complete structure sesquiterpenoid
Structure type: oligomer ; 907 [M+Na]
C
39H
64O
22Location inside paper: Fig. 3, Toxin c, tables 1,2,3
Compound class: glycoside
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606,IEDB_885812
Methods: 13C NMR, 1H NMR, FAB-MS, extraction, CI/D-MS
Synthetic data: biosynthesis
Comments, role: NMR temperature was not specified; although sugar 13C NMR referencing was reported as DSS at 0, CSDB staff suggested it was an error in Table 3 footnote, while the reference was 1,4-dioxane at 67.4
Related record ID(s): 44536, 44537
NCBI Taxonomy refs (TaxIDs): 48696
Show glycosyltransferases
NMR conditions: in D2O / (C)
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
2,5 bDGalf 107.9 82.0 77.3-77.4 83.5-83.6 71.3 63.6
2 bDGalf 106.9-107.3 81.9-82.0 77.1-77.2 82.2-82.3 76.7-76.9 62.0
13,5 bDGalf 107.9 82.0 77.3-77.4 83.5-83.6 71.3 63.6
13 bDGalf 106.9-107.3 81.9-82.0 77.1-77.2 82.2-82.3 76.7-76.9 62.0
Subst 49.0 75.4 43.0 147.5 44.0 22.7 35.8 25.7 36.5 36.0 149.3 114.9 71.5 108.6 16.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12
2,5 bDGalf
2 bDGalf
13,5 bDGalf
13 bDGalf
Subst 1.88 4.20 5.50 - 1.52 2.64 1.93 1.29 5.24-5.33 4.05-4.23 1.72 0.92
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12
2,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
2 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13,5 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
13 bDGalf NMR TSV error 2: unequal length of 13C and 1H datasets
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 |
|---|
| 2,5 | bDGalf | |
| 2 | bDGalf | |
| 13,5 | bDGalf | |
| 13 | bDGalf | |
| | Subst | 1.88 | 4.20 | 5.50 |
| 1.52 | 2.64 | 1.93 | 1.29 | 5.24
5.33 | 4.05
4.23 | 1.72 | 0.92 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 2,5 | bDGalf | 107.9 | 82.0 | 77.3
77.4 | 83.5
83.6 | 71.3 | 63.6 | |
| 2 | bDGalf | 106.9
107.3 | 81.9
82.0 | 77.1
77.2 | 82.2
82.3 | 76.7
76.9 | 62.0 | |
| 13,5 | bDGalf | 107.9 | 82.0 | 77.3
77.4 | 83.5
83.6 | 71.3 | 63.6 | |
| 13 | bDGalf | 106.9
107.3 | 81.9
82.0 | 77.1
77.2 | 82.2
82.3 | 76.7
76.9 | 62.0 | |
| | Subst | 49.0 | 75.4 | 43.0 | 147.5 | 44.0 | 22.7 | 35.8 | 25.7 | 36.5 | 36.0 | 149.3 | 114.9 | 71.5 | 108.6 | 16.9 |
|
There is only one chemically distinct structure:
Expand this record
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