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Tohyama S, Takahashi Y, Akamatsu Y
Biosynthesis of amycolamicin: The biosynthetic origin of a branched α-aminoethyl moiety in the unusual sugar amycolose
The Journal of Antibiotics 63(3) (2010)
147-149
|
b-D-Sugp
Sug = amycolose, 3C-α-aminoethyl-2,6-dideoxy-ribo-hexopyranose, 3C-α-aminoethyl-digitoxose = SMILES C{7}C(N)[C@]1(O)C{1}[C@H](O)O[C@H](C)[C@H]1O |
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Amycolatopsis sp. MK575-fF5
(Ancestor NCBI TaxID 37632,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
NCBI PubMed ID: 20111064Publication DOI: 10.1038/ja.2010.1Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Correspondence: tohyamas
bikaken.or.jp
Institutions: Microbial Chemistry Research Center, Microbial Chemistry Research Foundation, Tokyo, Japan
Amycolamicin is a new antibiotic, which has been isolated from the culture broth of Amycolatopsis sp. MK575-fF5 during our screening program for drug-resistant pathogens. Structurally, amycolamicin has unique features compared with other antibiotics; it contains trans-decalin, tetramic acid, two unusual sugars and pyrrole carbonic acid. Amycolamicin has bactericidal activity not only against a wide variety of bacteria but also against drug-resistant pathogens, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci, which are major pathogenic bacterial causes of hospital infections. There is a strong need to develop novel antibiotics with unique structures and modes of action because pathogens resistant to the ‘last resort’ antibiotic vancomycin have emerged. Judging from the present situation, amycolamicin could be considered as a potential candidate antibiotic
antibiotic, amycolamicin, amycolose, Amycolatopsis sp. MK575-fF5
Structure type: monomer
Location inside paper: Fig.1, 2
Trivial name: amycolose
Compound class: monosaccharide
Methods: 13C NMR, 1H NMR, IR, methanolysis, optical rotation measurement, isotopic labeling, cell growth, HR-ESI-MS, centrifugal partition chromatography
Synthetic data: enzymatic in vivo
Related record ID(s): 44009, 44011, 44012
NCBI Taxonomy refs (TaxIDs): 37632
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There is only one chemically distinct structure:
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Tohyama S, Takahashi Y, Akamatsu Y
Biosynthesis of amycolamicin: The biosynthetic origin of a branched α-aminoethyl moiety in the unusual sugar amycolose
The Journal of Antibiotics 63(3) (2010)
147-149
|
Subst-(6-7)-b-D-Sugp-(1-1)-Me
Subst = amycolamicin aglycon 1 = SMILES Cc1[nH]c({6}C(=O)O)c(Cl)c1Cl;
Sug = amycolose, 3C-α-aminoethyl-2,6-dideoxy-ribo-hexopyranose, 3C-α-aminoethyl-digitoxose = SMILES C{7}C(N)[C@]1(O)C{1}[C@H](O)O[C@H](C)[C@H]1O |
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Amycolatopsis sp. MK575-fF5
(Ancestor NCBI TaxID 37632,
species name lookup)
Taxonomic group: bacteria / Actinobacteria
(Phylum: Actinobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 20111064Publication DOI: 10.1038/ja.2010.1Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Correspondence: tohyamas
bikaken.or.jp
Institutions: Microbial Chemistry Research Center, Microbial Chemistry Research Foundation, Tokyo, Japan
Amycolamicin is a new antibiotic, which has been isolated from the culture broth of Amycolatopsis sp. MK575-fF5 during our screening program for drug-resistant pathogens. Structurally, amycolamicin has unique features compared with other antibiotics; it contains trans-decalin, tetramic acid, two unusual sugars and pyrrole carbonic acid. Amycolamicin has bactericidal activity not only against a wide variety of bacteria but also against drug-resistant pathogens, methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci, which are major pathogenic bacterial causes of hospital infections. There is a strong need to develop novel antibiotics with unique structures and modes of action because pathogens resistant to the ‘last resort’ antibiotic vancomycin have emerged. Judging from the present situation, amycolamicin could be considered as a potential candidate antibiotic
antibiotic, amycolamicin, amycolose, Amycolatopsis sp. MK575-fF5
Structure type: monomer ; 403.0788 [M+Na]+
C
15H
22Cl
2N
2O
5Location inside paper: Scheme 1, 3
Compound class: monosaccharide
Methods: 13C NMR, 1H NMR, IR, methanolysis, optical rotation measurement, isotopic labeling, cell growth, HR-ESI-MS, centrifugal partition chromatography
Synthetic data: enzymatic in vivo
Related record ID(s): 44009, 44010, 44012
NCBI Taxonomy refs (TaxIDs): 37632
Show glycosyltransferases
NMR conditions: in CDCl3
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
1,7 Subst 111.1-128.7 111.1-128.7 111.1-128.7 111.1-128.7 11.4 161.3
1 bDSugp 99.7 36.3 76.2 74.2 70.4 18.0 52.6 16.1
Me 55.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
1,7 Subst - - - - 2.28 -
1 bDSugp 4.69 1.49-1.92 - 3.17 3.64-4.42 1.34 ? 1.30
Me 3.48
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
1,7 Subst 11.4/2.28
1 bDSugp 99.7/4.69 36.3/1.49-1.92 74.2/3.17 70.4/3.64-4.42 18.0/1.34 52.6/? 16.1/1.30
Me 55.6/3.48
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 1,7 | Subst |
|
|
|
| 2.28 |
| |
| 1 | bDSugp | 4.69 | 1.49
1.92 |
| 3.17 | 3.64
4.42 | 1.34 | ? | 1.30 |
| | Me | 3.48 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 1,7 | Subst | 111.1
128.7 | 111.1
128.7 | 111.1
128.7 | 111.1
128.7 | 11.4 | 161.3 | |
| 1 | bDSugp | 99.7 | 36.3 | 76.2 | 74.2 | 70.4 | 18.0 | 52.6 | 16.1 |
| | Me | 55.6 | |
|
There is only one chemically distinct structure:
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Samanta S, Nandi AK, Sen IK, Maity P, Pattanayak M, Devi KS, Khatua S, Maiti TK, Acharya K, Islam SS
Studies on antioxidative and immunostimulating fucogalactan of the edible mushroom Macrolepiota dolichaula
Carbohydrate Research 413 (2015)
22-29
Macrolepiota dolichaula
(NCBI TaxID 190371,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
NCBI PubMed ID: 26074030Publication DOI: 10.1016/j.carres.2015.05.006Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Islam SS <sirajul_1999
yahoo.com>
Institutions: Department of Chemistry and Chemical Technology, Vidyasagar University, Midnapore, India, Department of Biotechnology, Indian Institute of Technology (IIT) Kharagpur, Kharagpur, India, Molecular and Applied Mycology and Plant Pathology Laboratory, Department of Botany, University of Calcutta, Kolkata, India
A water soluble fucogalactan (PS-II) of an average molecular weight 120000 Da was isolated from the aqueous extract of an edible mushroom Macrolepiota dolichaula. It was composed of fucose, galactose and 3-O-methyl galactose in a molar ratio of nearly 1:4:1. Structural characterization of PS-II was carried out using total hydrolysis, methylation analysis, Smith degradation, and 1D/2D NMR experiments. These results indicated that the proposed repeating unit of the PS-II had a backbone chain consisting of four (1→6)- linked α-D-Galp residues, one residue methylated at O-3, and another one substituted at O-2 by (1→2)-α-D-Galp residue, which is terminated with a α-l-Fucp moiety. The PS-II exhibited the antioxidant properties in different in vitro test systems, and also showed in vitro macrophage activation in RAW 264.7 cell line as well as splenocyte and thymocyte activation in mouse cell culture medium
NMR spectroscopy, Antioxidant, immunostimulation, fucogalactan, Macrolepiota dolichaula
Structure type: monomer
Location inside paper: Supplementary data, Table S1
Compound class: monosaccharide
Contained glycoepitopes: IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, acid hydrolysis, GLC, Smith degradation, HPLC, GPC, extraction, periodate oxidation, optical rotation measurement, acetylation, methylation analysis, reduction, column chromatography, precipitation, macrophage activity assay, phenol-sulfuric acid assay, radical scavenging assay, derivatization, Gerwig method, evaporation, centrifugation
Related record ID(s): 48444
NCBI Taxonomy refs (TaxIDs): 190371Reference(s) to other database(s): GTC:G96078VE
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NMR conditions: in D2O at 303(C) K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,3 Me 56.4
3 aDGalp 98.4 69.0 79.1 69.3 71.7 60.6
x?Gro 64.8 72.2 62.7
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,3 | Me | 56.4 | |
| 3 | aDGalp | 98.4 | 69.0 | 79.1 | 69.3 | 71.7 | 60.6 |
| | x?Gro | 64.8 | 72.2 | 62.7 | |
|
There is only one chemically distinct structure:
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