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Antimicrobial tunicamycin derivatives from the deep sea-derived SCSIO S15077.
Nat Prod Res
June 2020
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China.
Tunicamycin E (), featuring a methyl substitution at C-10', was isolated from marine-derived SCSIO S15077 originated from the South China Sea sediment together with six known compounds, tunicamycin B (), tunicamycin X (), tunicamycin A (), streptovirudin D (), tunicamycin C (), and tunicamycin C (). The structure of compound was elucidated by detailed spectroscopic data analyses. All the compounds exhibited strong to moderate antibacterial activity against Gram-positive bacteria BT01 and W102 with MIC values ranging from 0.
View Article and Find Full Text PDFLiquid chromatography-electrospray mass spectrometry of tunicamycin-type antibiotics.
Anal Biochem
February 2001
Department of Chemistry, State University of New York, College of Environmental Science and Forestry, 1 Forestry Drive, Syracuse, NY 13210, USA.
Several Streptomyces and Clavibacter species produce a family of tunicamycin-like antibiotics (tunicamycins, streptovirudins, corynetoxins, etc.) that inhibit the polyprenol-P:N-acetylhexosamine-1-P translocase family, thus blocking both bacterial cell wall biosynthesis and eukaryotic protein N-glycosylation. The mechanisms of biosynthesis and resistance to these toxins by the producing bacteria are largely unknown.
View Article and Find Full Text PDFThe synthesis of 5-C-(6-deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranos-6-yl)-2 ,3-O-isopropylidene-D-allo-pentofuranose [deaminotri-O-isopropylidene tunicamine].
Carbohydr Res
April 1992
Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw.
Three approaches to the synthesis of deaminotunicamine and derivatives were developed. Tin tetrachloride condensation of 6-deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galacto-heptodialdo-1, 5-pyranose with 2-(trimethylsilyloxy)furan gave a mixture of stereoisomeric precursors. Condensation of 1,2:3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranos e with the phosphate carbanion obtained from diethyl (2-furyl)methoxymethyl phosphonate led to 6-deoxy-7-C-(2-furyl)-1,2:3,4-di-O-isopropylidene-L-glycero-alpha-D- galactoheptopyranose (13).
View Article and Find Full Text PDFInhibitors of the biosynthesis and processing of N-linked oligosaccharides.
CRC Crit Rev Biochem
June 1984
A number of glycoproteins have oligosaccharides linked to protein in a GlcNAc----asparagine bond. These oligosaccharides may be either of the complex, the high-mannose or the hybrid structure. Each type of oligosaccharides is initially biosynthesized via lipid-linked oligosaccharides to form a Glc3Man9GlcNAc2-pyrophosphoryl-dolichol and transfer of this oligosaccharide to protein.
View Article and Find Full Text PDFTunicamycins, streptovirudins, and very recently, corynetoxins have been determined to be structurally related nucleoside antibiotics. Because of their special biological activity as inhibitors of protein glycosylation and their relatively complicated chemical structures, which differ from the common nucleoside antibiotics, they can be grouped together as a special subclass. A general specification system based on structural characteristics is included.
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