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Li J, Chen M, Hao X, Li S, Li F, Yu L, Xiao C, Gan M
Structural revision and absolute configuration of burnettramic acid A
Organic Letters 22(1) (2020)
98-101
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid A aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCCCC/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O |
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Aspergillus versicolor IMB17−055
(Ancestor NCBI TaxID 46472,
species name lookup)
Aspergillus chevalieri IMB18−208
(Ancestor NCBI TaxID 182096,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 31829608Publication DOI: 10.1021/acs.orglett.9b04008Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Gan M <ganml
imb.pumc.edu.cn>
Institutions: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
The recently discovered antibiotic burnettramic acid A (1) and three new congeners, burnettramic acids C-E (2-4), were identified from the co-cultures of two marine Aspergillus strains. The structure of burnettramic acid A was revised on the basis of reinterpretation of the nuclear magnetic resonance (NMR) data and chemical derivatization. The full absolute configurations of burnettramic acids were established using the Mosher ester method and Marfey's analysis, combined with density functional theory calculation of NMR and electric circular dichroism data.
NMR, absolute configuration, Aspergillus, burnettramic acids
Structure type: monomer ; 770.5055 [M+H]+, 792.4851 [M+Na]+
C
41H
71NO
12Location inside paper: FIg. 1, 1, supplementary materials, Table S1, Table S2
Trivial name: burnettramic acid A
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, antibacterial assay, HR-ESI-MS, derivatization, antifungal activity test, ECD, chiral LC-MS
Enzymes that release or process the structure: snailase
Related record ID(s): 50385, 50386, 50389, 50390, 50391
NCBI Taxonomy refs (TaxIDs): 46472,
182096Reference(s) to other database(s): GenDB:MN294469
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35
34 bDManp 101.7 72.6 75.2 68.4 78.2 62.8
Subst 178.0 103.8 196.4 35.7 17.7 42.1 30.9 20.2 37.8 28.0 31.0 30.7 30.3 30.8 33.8 134.0 127.6 41.8 72.5 37.6 22.9 38.4 72.4 38.5 26.9 30.7 30.7 27.2 30.9 70.6 198.2 67.5 37.7 74.3 53.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30 H31 H32 H33 H34 H35
34 bDManp 4.49 3.84 3.44 3.92 3.20 3.71-3.87
Subst - - - 3.79 1.11 1.37-1.55 1.43 0.89 1.08-1.35 1.24-1.32 1.25-1.35 1.25-1.35 1.29 1.36 2.01 5.47 5.45 2.15 3.55 1.36-1.50 1.36-1.59 1.37-1.45 3.51 1.37-1.42 1.34-1.45 1.33 1.35 1.39 1.61 3.53-3.91 - 4.25 1.60-2.11 4.60 3.10-3.88
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 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30 C31/H31 C32/H32 C33/H33 C34/H34 C35/H35
34 bDManp 101.7/4.49 72.6/3.84 75.2/3.44 68.4/3.92 78.2/3.20 62.8/3.71-3.87
Subst 35.7/3.79 17.7/1.11 42.1/1.37-1.55 30.9/1.43 20.2/0.89 37.8/1.08-1.35 28.0/1.24-1.32 31.0/1.25-1.35 30.7/1.25-1.35 30.3/1.29 30.8/1.36 33.8/2.01 134.0/5.47 127.6/5.45 41.8/2.15 72.5/3.55 37.6/1.36-1.50 22.9/1.36-1.59 38.4/1.37-1.45 72.4/3.51 38.5/1.37-1.42 26.9/1.34-1.45 30.7/1.33 30.7/1.35 27.2/1.39 30.9/1.61 70.6/3.53-3.91 67.5/4.25 37.7/1.60-2.11 74.3/4.60 53.8/3.10-3.88
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 | H31 | H32 | H33 | H34 | H35 |
|---|
| 34 | bDManp | 4.49 | 3.84 | 3.44 | 3.92 | 3.20 | 3.71
3.87 | |
| | Subst |
|
|
| 3.79 | 1.11 | 1.37
1.55 | 1.43 | 0.89 | 1.08
1.35 | 1.24
1.32 | 1.25
1.35 | 1.25
1.35 | 1.29 | 1.36 | 2.01 | 5.47 | 5.45 | 2.15 | 3.55 | 1.36
1.50 | 1.36
1.59 | 1.37
1.45 | 3.51 | 1.37
1.42 | 1.34
1.45 | 1.33 | 1.35 | 1.39 | 1.61 | 3.53
3.91 |
| 4.25 | 1.60
2.11 | 4.60 | 3.10
3.88 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 | C31 | C32 | C33 | C34 | C35 |
|---|
| 34 | bDManp | 101.7 | 72.6 | 75.2 | 68.4 | 78.2 | 62.8 | |
| | Subst | 178.0 | 103.8 | 196.4 | 35.7 | 17.7 | 42.1 | 30.9 | 20.2 | 37.8 | 28.0 | 31.0 | 30.7 | 30.3 | 30.8 | 33.8 | 134.0 | 127.6 | 41.8 | 72.5 | 37.6 | 22.9 | 38.4 | 72.4 | 38.5 | 26.9 | 30.7 | 30.7 | 27.2 | 30.9 | 70.6 | 198.2 | 67.5 | 37.7 | 74.3 | 53.8 |
|
There is only one chemically distinct structure:
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Li J, Chen M, Hao X, Li S, Li F, Yu L, Xiao C, Gan M
Structural revision and absolute configuration of burnettramic acid A
Organic Letters 22(1) (2020)
98-101
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid C aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(CCCN2C\1=O)[H])=O)C)CCCCCCC/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O |
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Aspergillus versicolor IMB17−055
(Ancestor NCBI TaxID 46472,
species name lookup)
Aspergillus chevalieri IMB18−208
(Ancestor NCBI TaxID 182096,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 31829608Publication DOI: 10.1021/acs.orglett.9b04008Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Gan M <ganml
imb.pumc.edu.cn>
Institutions: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
The recently discovered antibiotic burnettramic acid A (1) and three new congeners, burnettramic acids C-E (2-4), were identified from the co-cultures of two marine Aspergillus strains. The structure of burnettramic acid A was revised on the basis of reinterpretation of the nuclear magnetic resonance (NMR) data and chemical derivatization. The full absolute configurations of burnettramic acids were established using the Mosher ester method and Marfey's analysis, combined with density functional theory calculation of NMR and electric circular dichroism data.
NMR, absolute configuration, Aspergillus, burnettramic acids
Structure type: monomer ; 754.5102 [M+H]+, 776.4898 [M+Na]+
C
41H
71NO
11Location inside paper: FIg. 1, 2, supplementary materials, Table S3, 2
Trivial name: burnettramic acid C
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, antibacterial assay, HR-ESI-MS, derivatization, antifungal activity test, ECD, chiral LC-MS
Related record ID(s): 50388, 50390, 50391
NCBI Taxonomy refs (TaxIDs): 46472,
182096Reference(s) to other database(s): GenDB:MN294469
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35
34 bDManp 101.7 72.6 75.4 68.6 78.2 62.9
Subst 178.3 103.8 ? 36.2 17.8 42.1 31.9 20.2 38.0 28.1 31.0 30.7 30.3 30.9 33.8 134.0 127.7 41.7 72.5 37.7 22.9 38.4 72.4 38.5 26.8 30.6 30.6 27.2 30.9 68.6 198.4 68.9 28.2 28.0 44.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30 H31 H32 H33 H34 H35
34 bDManp 4.49 3.84 3.44 3.56 3.20 3.71-3.87
Subst - - - 3.79 1.09 1.35-1.54 1.42 0.88 1.08-1.34 1.23-1.32 1.25-1.35 1.25-1.35 1.28 1.35 2.00 5.46 5.44 2.15 3.54 1.37-1.49 1.34-1.59 1.39-1.47 3.52 1.36-1.42 1.34-1.45 1.32 1.34 1.39 1.60 3.53-3.90 - 3.97 1.46-2.14 2.06-2.11 3.21-3.64
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 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30 C31/H31 C32/H32 C33/H33 C34/H34 C35/H35
34 bDManp 101.7/4.49 72.6/3.84 75.4/3.44 68.6/3.56 78.2/3.20 62.9/3.71-3.87
Subst 36.2/3.79 17.8/1.09 42.1/1.35-1.54 31.9/1.42 20.2/0.88 38.0/1.08-1.34 28.1/1.23-1.32 31.0/1.25-1.35 30.7/1.25-1.35 30.3/1.28 30.9/1.35 33.8/2.00 134.0/5.46 127.7/5.44 41.7/2.15 72.5/3.54 37.7/1.37-1.49 22.9/1.34-1.59 38.4/1.39-1.47 72.4/3.52 38.5/1.36-1.42 26.8/1.34-1.45 30.6/1.32 30.6/1.34 27.2/1.39 30.9/1.60 68.6/3.53-3.90 68.9/3.97 28.2/1.46-2.14 28.0/2.06-2.11 44.3/3.21-3.64
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 | H31 | H32 | H33 | H34 | H35 |
|---|
| 34 | bDManp | 4.49 | 3.84 | 3.44 | 3.56 | 3.20 | 3.71
3.87 | |
| | Subst |
|
|
| 3.79 | 1.09 | 1.35
1.54 | 1.42 | 0.88 | 1.08
1.34 | 1.23
1.32 | 1.25
1.35 | 1.25
1.35 | 1.28 | 1.35 | 2.00 | 5.46 | 5.44 | 2.15 | 3.54 | 1.37
1.49 | 1.34
1.59 | 1.39
1.47 | 3.52 | 1.36
1.42 | 1.34
1.45 | 1.32 | 1.34 | 1.39 | 1.60 | 3.53
3.90 |
| 3.97 | 1.46
2.14 | 2.06
2.11 | 3.21
3.64 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 | C31 | C32 | C33 | C34 | C35 |
|---|
| 34 | bDManp | 101.7 | 72.6 | 75.4 | 68.6 | 78.2 | 62.9 | |
| | Subst | 178.3 | 103.8 | ? | 36.2 | 17.8 | 42.1 | 31.9 | 20.2 | 38.0 | 28.1 | 31.0 | 30.7 | 30.3 | 30.9 | 33.8 | 134.0 | 127.7 | 41.7 | 72.5 | 37.7 | 22.9 | 38.4 | 72.4 | 38.5 | 26.8 | 30.6 | 30.6 | 27.2 | 30.9 | 68.6 | 198.4 | 68.9 | 28.2 | 28.0 | 44.3 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Li J, Chen M, Hao X, Li S, Li F, Yu L, Xiao C, Gan M
Structural revision and absolute configuration of burnettramic acid A
Organic Letters 22(1) (2020)
98-101
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid D aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCC/C=C/C=C/C{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O |
Show graphically |
Aspergillus versicolor IMB17−055
(Ancestor NCBI TaxID 46472,
species name lookup)
Aspergillus chevalieri IMB18−208
(Ancestor NCBI TaxID 182096,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 31829608Publication DOI: 10.1021/acs.orglett.9b04008Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Gan M <ganml
imb.pumc.edu.cn>
Institutions: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
The recently discovered antibiotic burnettramic acid A (1) and three new congeners, burnettramic acids C-E (2-4), were identified from the co-cultures of two marine Aspergillus strains. The structure of burnettramic acid A was revised on the basis of reinterpretation of the nuclear magnetic resonance (NMR) data and chemical derivatization. The full absolute configurations of burnettramic acids were established using the Mosher ester method and Marfey's analysis, combined with density functional theory calculation of NMR and electric circular dichroism data.
NMR, absolute configuration, Aspergillus, burnettramic acids
Structure type: monomer ; 768.4890 [M+H]+, 790.4727 [M+Na]+
C
41H
69NO
12Location inside paper: FIg. 1, 3, supplementary materials, Table S3, 3
Trivial name: burnettramic acid D
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, antibacterial assay, HR-ESI-MS, derivatization, antifungal activity test, ECD, chiral LC-MS
Related record ID(s): 50388, 50389, 50391
NCBI Taxonomy refs (TaxIDs): 46472,
182096Reference(s) to other database(s): GenDB:MN294469
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35
34 bDManp 101.8 72.6 75.4 68.6 78.3 62.9
Subst ? 103.9 ? 38.8 18.0 42.1 31.9 20.3 38.3 28.0 30.6 30.6 33.7 133.8 131.8 134.1 129.1 41.8 72.5 37.9 22.9 38.4 72.4 38.5 26.8 30.9 30.6 27.2 30.8 70.7 ? 67.0 38.3 74.5 54.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30 H31 H32 H33 H34 H35
34 bDManp 4.49 3.84 3.44 3.56 3.20 3.71-3.86
Subst - - - 3.85 1.00 1.23-1.51 1.41 0.86 1.08-1.34 1.23-1.31 1.26 1.36 2.03 5.56 5.99 6.04 5.58 2.20 3.59 1.37-1.49 1.36-1.59 1.36-1.45 3.51 1.37-1.42 1.37-1.45 1.33 1.35 1.38 1.61 3.53-3.91 - 4.09 1.53-2.09 4.53 3.03-3.81
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 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30 C31/H31 C32/H32 C33/H33 C34/H34 C35/H35
34 bDManp 101.8/4.49 72.6/3.84 75.4/3.44 68.6/3.56 78.3/3.20 62.9/3.71-3.86
Subst 38.8/3.85 18.0/1.00 42.1/1.23-1.51 31.9/1.41 20.3/0.86 38.3/1.08-1.34 28.0/1.23-1.31 30.6/1.26 30.6/1.36 33.7/2.03 133.8/5.56 131.8/5.99 134.1/6.04 129.1/5.58 41.8/2.20 72.5/3.59 37.9/1.37-1.49 22.9/1.36-1.59 38.4/1.36-1.45 72.4/3.51 38.5/1.37-1.42 26.8/1.37-1.45 30.9/1.33 30.6/1.35 27.2/1.38 30.8/1.61 70.7/3.53-3.91 67.0/4.09 38.3/1.53-2.09 74.5/4.53 54.0/3.03-3.81
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 | H31 | H32 | H33 | H34 | H35 |
|---|
| 34 | bDManp | 4.49 | 3.84 | 3.44 | 3.56 | 3.20 | 3.71
3.86 | |
| | Subst |
|
|
| 3.85 | 1.00 | 1.23
1.51 | 1.41 | 0.86 | 1.08
1.34 | 1.23
1.31 | 1.26 | 1.36 | 2.03 | 5.56 | 5.99 | 6.04 | 5.58 | 2.20 | 3.59 | 1.37
1.49 | 1.36
1.59 | 1.36
1.45 | 3.51 | 1.37
1.42 | 1.37
1.45 | 1.33 | 1.35 | 1.38 | 1.61 | 3.53
3.91 |
| 4.09 | 1.53
2.09 | 4.53 | 3.03
3.81 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 | C31 | C32 | C33 | C34 | C35 |
|---|
| 34 | bDManp | 101.8 | 72.6 | 75.4 | 68.6 | 78.3 | 62.9 | |
| | Subst | ? | 103.9 | ? | 38.8 | 18.0 | 42.1 | 31.9 | 20.3 | 38.3 | 28.0 | 30.6 | 30.6 | 33.7 | 133.8 | 131.8 | 134.1 | 129.1 | 41.8 | 72.5 | 37.9 | 22.9 | 38.4 | 72.4 | 38.5 | 26.8 | 30.9 | 30.6 | 27.2 | 30.8 | 70.7 | ? | 67.0 | 38.3 | 74.5 | 54.0 |
|
The spectrum also has 3 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Li J, Chen M, Hao X, Li S, Li F, Yu L, Xiao C, Gan M
Structural revision and absolute configuration of burnettramic acid A
Organic Letters 22(1) (2020)
98-101
|
b-D-Manp-(1-34)-Subst
Subst = burnettramic acid E aglycon = SMILES C[C@@H](C[C@@H](/{9}C(O)=C1C([C@]2(C{1}[C@@H](O)CN2C\1=O)[H])=O)C)CCCCCCCCCC{23}[C@@H](CCC{27}[C@@H](CCCCCC{34}CO)O)O |
Show graphically |
Aspergillus versicolor IMB17−055
(Ancestor NCBI TaxID 46472,
species name lookup)
Aspergillus chevalieri IMB18−208
(Ancestor NCBI TaxID 182096,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 31829608Publication DOI: 10.1021/acs.orglett.9b04008Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Gan M <ganml
imb.pumc.edu.cn>
Institutions: Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China
The recently discovered antibiotic burnettramic acid A (1) and three new congeners, burnettramic acids C-E (2-4), were identified from the co-cultures of two marine Aspergillus strains. The structure of burnettramic acid A was revised on the basis of reinterpretation of the nuclear magnetic resonance (NMR) data and chemical derivatization. The full absolute configurations of burnettramic acids were established using the Mosher ester method and Marfey's analysis, combined with density functional theory calculation of NMR and electric circular dichroism data.
NMR, absolute configuration, Aspergillus, burnettramic acids
Structure type: monomer ; 772.5210 [M+H]+, 794.5015 [M+Na]+
C
41H
73NO
12Location inside paper: FIg. 1, 4, supplementary materials, Table S3, 4
Trivial name: burnettramic acid E
Compound class: glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72
Methods: 13C NMR, 1H NMR, NMR-2D, antibacterial assay, HR-ESI-MS, derivatization, antifungal activity test, ECD, chiral LC-MS
Related record ID(s): 50388, 50389, 50390
NCBI Taxonomy refs (TaxIDs): 46472,
182096Reference(s) to other database(s): GenDB:MN294469
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32 C33 C34 C35
34 bDManp 101.8 72.6 75.4 68.6 78.3 62.9
Subst 178.3 103.7 ? 36.4 17.8 42.1 31.9 20.2 38.0 28.1 31.0 30.8-31.0 30.8-31.0 30.8-31.0 30.8-31.0 30.8-31.0 26.8 37.9 72.4 38.5 23.0 38.5 72.4 38.0 26.9 30.8-30.9 30.6 27.2 30.8 70.7 ? 67.3 37.9 74.3 53.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30 H31 H32 H33 H34 H35
34 bDManp 4.49 3.84 3.44 3.56 3.20 3.71-3.86
Subst - - - 3.79 1.08 1.34-1.54 1.42 0.88 1.08-1.35 1.23-1.31 1.25-1.35 1.25-1.35 1.25-1.35 1.25-1.35 1.25-1.35 1.25-1.35 1.33-1.45 1.37-1.45 3.52 1.38-1.48 1.37-1.59 1.37-1.45 3.52 1.37-1.42 1.33-1.45 1.33 1.33 1.39 1.60 3.54-3.91 - 4.22 1.58-2.10 4.58 3.08-3.86
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 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30 C31/H31 C32/H32 C33/H33 C34/H34 C35/H35
34 bDManp 101.8/4.49 72.6/3.84 75.4/3.44 68.6/3.56 78.3/3.20 62.9/3.71-3.86
Subst 36.4/3.79 17.8/1.08 42.1/1.34-1.54 31.9/1.42 20.2/0.88 38.0/1.08-1.35 28.1/1.23-1.31 31.0/1.25-1.35 30.8-31.0/1.25-1.35 30.8-31.0/1.25-1.35 30.8-31.0/1.25-1.35 30.8-31.0/1.25-1.35 30.8-31.0/1.25-1.35 26.8/1.33-1.45 37.9/1.37-1.45 72.4/3.52 38.5/1.38-1.48 23.0/1.37-1.59 38.5/1.37-1.45 72.4/3.52 38.0/1.37-1.42 26.9/1.33-1.45 30.8-30.9/1.33 30.6/1.33 27.2/1.39 30.8/1.60 70.7/3.54-3.91 67.3/4.22 37.9/1.58-2.10 74.3/4.58 53.8/3.08-3.86
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 | H31 | H32 | H33 | H34 | H35 |
|---|
| 34 | bDManp | 4.49 | 3.84 | 3.44 | 3.56 | 3.20 | 3.71
3.86 | |
| | Subst |
|
|
| 3.79 | 1.08 | 1.34
1.54 | 1.42 | 0.88 | 1.08
1.35 | 1.23
1.31 | 1.25
1.35 | 1.25
1.35 | 1.25
1.35 | 1.25
1.35 | 1.25
1.35 | 1.25
1.35 | 1.33
1.45 | 1.37
1.45 | 3.52 | 1.38
1.48 | 1.37
1.59 | 1.37
1.45 | 3.52 | 1.37
1.42 | 1.33
1.45 | 1.33 | 1.33 | 1.39 | 1.60 | 3.54
3.91 |
| 4.22 | 1.58
2.10 | 4.58 | 3.08
3.86 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 | C31 | C32 | C33 | C34 | C35 |
|---|
| 34 | bDManp | 101.8 | 72.6 | 75.4 | 68.6 | 78.3 | 62.9 | |
| | Subst | 178.3 | 103.7 | ? | 36.4 | 17.8 | 42.1 | 31.9 | 20.2 | 38.0 | 28.1 | 31.0 | 30.8
31.0 | 30.8
31.0 | 30.8
31.0 | 30.8
31.0 | 30.8
31.0 | 26.8 | 37.9 | 72.4 | 38.5 | 23.0 | 38.5 | 72.4 | 38.0 | 26.9 | 30.8
30.9 | 30.6 | 27.2 | 30.8 | 70.7 | ? | 67.3 | 37.9 | 74.3 | 53.8 |
|
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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