Diastereoselective Total Synthesis and Structural Confirmation of Surugamide F

Kuranaga, Takefumi; Fukuba, Atsuki; Ninomiya, Akihiro; Takada, Kentaro; Matsunaga, Shigeki; Wakimoto, Toshiyuki

doi:10.1248/cpb.c18-00072

Cited by 11 publications

(4 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Surugamide F (43, Table 1) is a linear decapeptide also isolated from marine Streptomyces sp. JAMM992 [69,70]. Surugamides have not been initially reported as antibiotics until surugamide A was reisolated from Streptomyces sp.…”

Section: Surugamidesmentioning

confidence: 99%

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Wang,

Gu,

Wang

et al. 2023

Marine Drugs

View full text Add to dashboard Cite

In the post-antibiotic era, the rapid development of antibiotic resistance and the shortage of available antibiotics are triggering a new health-care crisis. The discovery of novel and potent antibiotics to extend the antibiotic pipeline is urgent. Small-molecule antimicrobial peptides have a wide variety of antimicrobial spectra and multiple innovative antimicrobial mechanisms due to their rich structural diversity. Consequently, they have become a new research hotspot and are considered to be promising candidates for next-generation antibiotics. Therefore, we have compiled a collection of small-molecule antimicrobial peptides derived from marine microorganisms from the last fifteen years to show the recent advances in this field. We categorize these compounds into three classes—cyclic oligopeptides, cyclic depsipeptides, and cyclic lipopeptides—according to their structural features, and present their sources, structures, and antimicrobial spectrums, with a discussion of the structure activity relationships and mechanisms of action of some compounds.

show abstract

Section: Surugamidesmentioning

confidence: 99%

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Wang,

Gu,

Wang

et al. 2023

Marine Drugs

View full text Add to dashboard Cite

show abstract

“…Surugamide derivatives were found in seven Streptomyces strains: PTE-035, PTE-036, PTE-040, PTE-045, PTE-050, PTE-054, and PTE-064. To date, there are only five surugamides described in the literature [51,71]. The surugamide family contains several unknown derivatives (Figure 7A), thus suggesting that these actinomycetes are a promising source of new compounds to be further investigated.…”

Section: Ms/ms-based Molecular Networkingmentioning

confidence: 99%

The Diversity, Metabolomics Profiling, and the Pharmacological Potential of Actinomycetes Isolated from the Estremadura Spur Pockmarks (Portugal)

et al. 2021

View full text Add to dashboard Cite

The Estremadura Spur pockmarks are a unique and unexplored ecosystem located in the North Atlantic, off the coast of Portugal. A total of 85 marine-derived actinomycetes were isolated and cultured from sediments collected from this ecosystem at a depth of 200 to 350 m. Nine genera, Streptomyces, Micromonospora, Saccharopolyspora, Actinomadura, Actinopolymorpha, Nocardiopsis, Saccharomonospora, Stackebrandtia, and Verrucosispora were identified by 16S rRNA gene sequencing analyses, from which the first two were the most predominant. Non-targeted LC-MS/MS, in combination with molecular networking, revealed high metabolite diversity, including several known metabolites, such as surugamide, antimycin, etamycin, physostigmine, desferrioxamine, ikarugamycin, piericidine, and rakicidin derivatives, as well as numerous unidentified metabolites. Taxonomy was the strongest parameter influencing the metabolite production, highlighting the different biosynthetic potentials of phylogenetically related actinomycetes; the majority of the chemical classes can be used as chemotaxonomic markers, as the metabolite distribution was mostly genera-specific. The EtOAc extracts of the actinomycete isolates demonstrated antimicrobial and antioxidant activity. Altogether, this study demonstrates that the Estremadura Spur is a source of actinomycetes with potential applications for biotechnology. It highlights the importance of investigating actinomycetes from unique ecosystems, such as pockmarks, as the metabolite production reflects their adaptation to this habitat.

show abstract

“…We therefore recon rmed the absolute con guration of surugamide F by diastereoselective total synthesis (Scheme 1). 22 To prepare the optically pure AMPA residue, Evans asymmetric alkylation 23 of propionyl oxazolidinone with BOMCl was carried out. The removal of the benzyl group of 8a afforded a primary alcohol 9a, which was further converted to an amine 10a.…”

Section: Total Synthesis Of Surugamide Fmentioning

confidence: 99%

A New Cyclase Family Catalyzing Head-to-Tail Macrolactamization of Non-ribosomal Peptides

Matsuda

Kuranaga

Wakimoto

2019

J. Synth. Org. Chem. Jpn.

Self Cite

View full text Add to dashboard Cite

Macrolactamization is one of the most important peptide modifying reactions. However, chemical macrocyclization is often hampered by several technical problems such as epimerization at the C terminal residue, and a requirement for high dilution conditions, as well as for protective groups. In contrast, natural cyclopeptides are biosynthesized by ef cient cyclases under mild conditions, suggesting these enzymes have potential as biocatalysts. However, the versatility of natural cyclases has not been fully exploited, mainly due to their strict substrate speci city. During the course of our synthetic and biosynthetic studies on surugamides, we have discovered a new family of cyclases showing broad substrate speci city. The new cyclase SurE, which is homologous to penicillin binding protein, of oads two assembly lines of non ribosomal peptide synthetase, and remarkably, catalyzes the head to tail macrolactamization of two distinct peptides, thereby offering a new platform for the development of biocatalysts for macrolactamization.

show abstract

Diastereoselective Total Synthesis and Structural Confirmation of Surugamide F

Cited by 11 publications

References 13 publications

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

The Diversity, Metabolomics Profiling, and the Pharmacological Potential of Actinomycetes Isolated from the Estremadura Spur Pockmarks (Portugal)

A New Cyclase Family Catalyzing Head-to-Tail Macrolactamization of Non-ribosomal Peptides

Contact Info

Product

Resources

About