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1. (Article ID: 5287)
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
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
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
Methods: 13C NMR, 1H NMR, IR, methanolysis, optical rotation measurement, isotopic labeling, cell growth, HR-ESI-MS, centrifugal partition chromatography
The publication contains the following compound(s):
- Compound ID: 13321
|
Subst1-(6-7)-b-D-Sugp-(1-6)-Subst2-(1-1)-b-L-6dAllp1N2Me3Ac4Cm
Subst1 = 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;
Subst2 = amycolamicin aglycon 2 = SMILES C=C2CC{6}[C@@H](O)[C@@H]3/C=C\[C@H](C)[C@H](C(=O)/C1=C(O)/{1}C(C(C)C)NC1=O)[C@@H]23 |
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Structure type: monomer
Trivial name: amycolamicin
Compound class: glycoside
- Compound ID: 13322
|
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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Structure type: monomer
Trivial name: amycolose
- Compound ID: 13323
|
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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Structure type: monomer
; 403.0788 [M+Na]+
C15H22Cl2N2O5
- Compound ID: 13324
|
Subst-(6-7)-a-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 |
Show graphically |
Structure type: monomer
; 403.0787 [M+Na]+
C15H22Cl2N2O5
Compound class: glycoside
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