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Genomics-Driven Discovery of Chlorinated Cyclic Hexapeptides Ulleungmycins A and B from a Streptomyces Species
- Source :
- Journal of Natural Products. 80:3025-3031
- Publication Year :
- 2017
- Publisher :
- American Chemical Society (ACS), 2017.
-
Abstract
- Analysis of the genome sequence of Streptomyces sp. KCB13F003 showed the presence of a cryptic gene cluster encoding flavin-dependent halogenase and nonribosomal peptide synthetase. Pleiotropic approaches using multiple culture media followed by LC-MS-guided isolation and spectroscopic analysis enabled the identification of two new chlorinated cyclic hexapeptides, ulleungmycins A and B (1 and 2). Their structures, including absolute configurations, were determined by 1D and 2D NMR techniques, advanced Marfey's analysis, and GITC derivatization. The new peptides, featuring unusual amino acids 5-chloro-l-tryptophan and d-homoleucine, exhibited moderate antibacterial activities against Gram-positive pathogenic bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus.
- Subjects :
- Methicillin-Resistant Staphylococcus aureus
0301 basic medicine
Staphylococcus aureus
Stereochemistry
030106 microbiology
Pharmaceutical Science
Microbial Sensitivity Tests
Gram-Positive Bacteria
medicine.disease_cause
Peptides, Cyclic
01 natural sciences
Streptomyces
Analytical Chemistry
03 medical and health sciences
Nonribosomal peptide
Flavins
Drug Discovery
Gene cluster
Hydrocarbons, Chlorinated
medicine
Amino Acid Sequence
Peptide Synthases
Nuclear Magnetic Resonance, Biomolecular
Peptide sequence
Pharmacology
chemistry.chemical_classification
Whole genome sequencing
Molecular Structure
biology
010405 organic chemistry
Organic Chemistry
Tryptophan
Pathogenic bacteria
Genomics
Staphylococcal Infections
biology.organism_classification
Anti-Bacterial Agents
0104 chemical sciences
Amino acid
Complementary and alternative medicine
chemistry
Biochemistry
Molecular Medicine
Methicillin Resistance
Oxidoreductases
Two-dimensional nuclear magnetic resonance spectroscopy
Chromatography, Liquid
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 80
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi.dedup.....dc0db3b845900a5a8efffd954de0b50f