Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp

  title={Thalassospiramide G, a New $\gamma$-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp},
  author={S. Um and Y. Pyee and Eun-hee Kim and S. Lee and Jongheon Shin and D. Oh},
  journal={Marine Drugs},
  pages={611 - 622}
In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2–3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy-penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl)ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of… Expand
Thalassosamide, a Siderophore Discovered from the Marine-Derived Bacterium Thalassospira profundimaris.
The rapid identification and prioritization of novel active marine natural products using an improved dereplication strategy using thalassosamide, a new cyclic trihydroxamate compound discovered from the α-proteobacterium Thalassospira profundimaris, is described. Expand
A marine algicidal Thalassospira and its active substance against the harmful algal bloom species Karenia mikimotoi
This study is the first to report benzoic acid activity against K. mikimotoi as well as production of benzoIC acid by a Thalassospira species. Expand
Multilocus Sequence Analysis for Assessment of Phylogenetic Diversity and Biogeography in Thalassospira Bacteria from Diverse Marine Environments
The phylogenetic analyses and biogeography of the Thalassospira bacteria were systematically investigated for the first time and will be helpful to explore further their ecological role and adaptive evolution in marine environments. Expand
Mechanism of Action of Thalassospiramides, A New Class of Calpain Inhibitors
Using a combination of chemical modifications, mass spectrometric techniques, site-directed mutagenesis, and molecular modeling, the covalent binding of thalassospiramide's α,β-unsaturated carbonyl moiety to the thiol group of calpain's catalytic Cys115 residue by a Michael 1,4-addition reaction is shown. Expand
Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies
This review will focus on genomics driven approaches to understanding the biosynthetic mechanisms for natural products produced by marine proteobacteria. Expand
Ribosomal Elongation of Cyclic γ-Amino Acids using a Reprogrammed Genetic Code.
  • T. Katoh, H. Suga
  • Chemistry, Medicine
  • Journal of the American Chemical Society
  • 2020
It is shown that the combination of elongation factor P and engineered tRNAs improves cyclic γ-amino acid incorporation efficiency and should be applicable to in vitro screening methodologies such as mRNA display for discovering novel peptide drugs. Expand
22 The Family Rhodospirillaceae
The genus Azospirillum contains several diazotrophic, plant-associated bacteria having plant growthpromoting potential with agricultural application and other genera include strains with interesting biotechnological potentials. Expand
Targeted metagenomics as a tool to tap into marine natural product diversity for the discovery and production of drug candidates
This review explores specific obstacles that have led to the low success rate of metagenomic screening for marine drug discovery and presents how targeted and function-guided strategies, employing modern, and multi-disciplinary approaches have yielded some of the most exciting discoveries attributed to uncultured marine bacteria. Expand
Peptides, Peptidomimetics, and Polypeptides from Marine Sources: A Wealth of Natural Sources for Pharmaceutical Applications
This review focuses on some of the peptides derived from marine sources in the past ten years and gives a brief review of those that are currently in clinical trials or on the market. Expand
Antimicrobial and Immunomodulatory Properties and Applications of Marine-Derived Proteins and Peptides
This review provides a comprehensive overview of marine immunomodulatory proteins, peptides, and protein hydrolysates as well as their production, mechanisms of action, and applications in human therapy. Expand


Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species. I. Taxonomy, fermentation, isolation and biological activities
Seven novel maleimide derivatives named aqabamycin A, B, C, D, E, F and G are described here for the first time from a natural source and vibrindole A was found to have cytotoxic activity. Expand
Aqabamycins A–G: novel nitro maleimides from a marine Vibrio species: II. Structure elucidation*
The structures of secondary metabolites with antibacterial and cytotoxic activities produced by a marine Vibrio strain from the Red Sea were elucidated using NMR, MS spectra and by comparison with synthetic material. Expand
Loihichelins A-F, a suite of amphiphilic siderophores produced by the marine bacterium Halomonas LOB-5.
A suite of amphiphilic siderophores, loihichelins A-F, were isolated from cultures of the marine bacterium Halomonas sp. LOB-5. This heterotrophic Mn(II)-oxidizing bacterium was recently isolatedExpand
Biosynthetic multitasking facilitates thalassospiramide structural diversity in marine bacteria.
The discovery and characterization of an extended family of 14 new analogues from four Tistrella and Thalassospira isolates that belong to six structure classes in which the length and composition of the acylpeptide side chain varies extensively are described. Expand
Cyclic tetrapeptides from marine bacteria associated with the seaweed Diginea sp.and the sponge Halisarca ectofibrosa
Abstract A Pseudomonas sp. was cultured which was associated with the Japanese seaweed Diginea sp. Crude extracts prepared from this bacterial culture were found to inhibit the growth of other marineExpand
Thalassospiramides A and B, immunosuppressive peptides from the marine bacterium Thalassospira sp.
Two new cyclic peptides were isolated from a new member of the marine alpha-proteobacterium Thalassospira and bear unusual gamma-amino acids and show immunosuppressive activity in an interleukin-5 production inhibition assay. Expand
Almazole C, a New Indole Alkaloid Bearing an Unusually 2,5-Disubstituted Oxazole Moiety, and its putative biogenetic peptidic precursors, from a senegalese delesseriacean seaweed†
From product isolation and biomimetic synthesis – which also establishes absolute configurations – the known oxazole alkaloids almazoles A ((+)-1) and B ((+)-2) seem to arise in a SenegaleseExpand
Vanchrobactin and anguibactin siderophores produced by Vibrio sp. DS40M4.
The marine bacterium Vibrio sp. DS40M4 has been found to produce a new triscatechol amide siderophore, trivanchrobactin (1), a related new biscatecholamide compound, divanchrobactin (2), and theExpand
B-90063, a novel endothelin converting enzyme inhibitor isolated from a new marine bacterium, Blastobacter sp. SANK 71894.
A novel endothelin-converting enzyme (ECE) inhibitor, B-90063, was isolated from the culture supernatant of the newly discovered marine bacterium Blastobacter sp. SANK 71894. Based on spectralExpand
The isolation, purification and biological activity of a novel antibacterial compound produced by Pseudomonas stutzeri.
It could be demonstrated that a purified solution of zafrin was active against several human pathogens, including Staphylococcus aureus, and Salmonella typhi, and did not inhibit the growth of eukaryotic organisms Candida albicans and Schizosaccharomyces pombe. Expand