Polydiscamide A: a new bioactive depsipeptide from the marine sponge Discodermia sp

Gulavita, Nanda K.; Gunasekera, Sarath P.; Pomponi, Shirley A.; Robinson, Elise V.

doi:10.1021/jo00032a031

Cited by 72 publications

(45 citation statements)

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“…[96] Recently, Minales group has reported a series of cyclic depsipeptides from a New Caledonian species of Callipelta. The structural elucidations of callipeltins A (48) B, and C, which possess anti-HIV, antifungal, and cytotoxicity activities, revealed a side chain that terminated with an unusual polypropionate moiety.…”

Section: Cyclic Depsipeptidesmentioning

confidence: 99%

Lithistid Sponges: Star Performers or Hosts to the Stars

Bewley

Faulkner

1998

Angewandte Chemie International Edition

190

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Extremely careful separation of the symbiotic bacteria from the cells of lithistid sponges has provided evidence that in the case of Theonella swinhoei the chemically diverse and biologically active metabolites, swinholide A and theopalauamide (1), are produced by symbionts. Marine sponges of the order Lithistida contain a diverse range of exotic natural products with valuable biological and pharmacological activities.

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Section: Cyclic Depsipeptidesmentioning

confidence: 99%

Lithistid Sponges: Star Performers or Hosts to the Stars

Bewley

Faulkner

1998

Angewandte Chemie International Edition

190

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“…Some of them are used in the clinic, e.g., gramicidin S and tyrocidine with bactericidal activity, while others are in clinical trials, e.g., dehydrodidemnin B, and most of them originate from natural resources. Although the literature is enriched with reports concerned with marine-derived linear proline-rich bioactive peptides [1,2,3,4,5], e.g., dolastatin 15, kurahyne B, jahanyne, cemadotin, koshikamide A 1 , etc., PRCPs from marine resources are becoming popular and attracting the attention of scientists nowadays, due to their unique structural features and a wide range of the biological properties, like cytotoxicity [6], antibacterial activity [7], antifungal activity [8], immunosuppressive activity [9], anti-inflammatory activity [10], anti-HIV activity [11], repellent (antifouling) activity [12], antitubercular activity [13] and antiviral activity [14], associated with them. PRCPs include a large and heterogeneous group of small to large-sized oligopeptides characterized by the presence of proline units often constituting peculiar sequences, which confers them a typical structure that determines the various biological functions endowed by these molecules.…”

Section: Introductionmentioning

confidence: 99%

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

et al. 2016

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Peptides have gained increased interest as therapeutics during recent years. More than 60 peptide drugs have reached the market for the benefit of patients and several hundreds of novel therapeutic peptides are in preclinical and clinical development. The key contributor to this success is the potent and specific, yet safe, mode of action of peptides. Among the wide range of biologically-active peptides, naturally-occurring marine-derived cyclopolypeptides exhibit a broad range of unusual and potent pharmacological activities. Because of their size and complexity, proline-rich cyclic peptides (PRCPs) occupy a crucial chemical space in drug discovery that may provide useful scaffolds for modulating more challenging biological targets, such as protein-protein interactions and allosteric binding sites. Diverse pharmacological activities of natural cyclic peptides from marine sponges, tunicates and cyanobacteria have encouraged efforts to develop cyclic peptides with well-known synthetic methods, including solid-phase and solution-phase techniques of peptide synthesis. The present review highlights the natural resources, unique structural features and the most relevant biological properties of proline-rich peptides of marine-origin, focusing on the potential therapeutic role that the PRCPs may play as a promising source of new peptide-based novel drugs.

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“…L- tert -Leucine ( 1a ) and L- tert -amylglycine (β-methylisoleucine, 1b ) occur in the 48-mers polytheonamides A and B; two highly cytotoxic β-helix, membrane-pore forming peptides from the marine sponge, Theonella swinhoei 4. The peptides polydiscamide A from Discodermia 5a ( 2 , Figure 1), and the polydiscamides B–C from the sponge Ircinia ,5b which are the first non-endogenous inhibitors of sensory neuron-specific G-protein coupled receptors (SNSRs), also contain 1a and 1b 6. The amino acid γ-hydroxy- tert -leucine (L-pantonine, 1c ) was proposed as an intermediate in the biosynthesis of pantoic acid 7.…”

mentioning

confidence: 99%

Diastereoselective Allylstannane Additions to (S)-5,6-Dihydro-2H-5-phenyloxazin-2-one. A Concise Synthesis of (S)-β-Methylisoleucine

Pigza

Molinski

2010

Org. Lett.

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The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2 H-oxazinone (3) was achieved under Brønsted acid catalysistogive 2-allylmorpholinones with high diastereoselectivity (up to dr14.2:1).The product of dimethylallyltributylstannane addition to 3 was converted to L-β-methylisoleucine, an α-amino acid residue found in the complex, biologically-active marine-derived peptides polytheonamides A and B and polydiscamides A-C.Marine peptides often contain highly modified amino acids, including chlorinated amino acids, 1 β-amino acids 2 and highly-substituted β,β-dimethyl-α-amino acids. 3 L-tert-Leucine (1a) and L-tert-amylglycine (β-methylisoleucine, 1b) occur in the 48-mers polytheonamides A and B; two highly cytotoxic β-helix, membrane-pore forming peptides from the marine sponge, Theonella swinhoei. 4 The peptides polydiscamide A from Discodermia 5a (2 , Figure 1), and the polydiscamides B-C from the sponge Ircinia ,5b which are the first non-endogenous inhibitors of sensory neuron-specific G-protein coupled receptors (SNSRs), also contain 1a and 1b. 6 The amino acid γ-hydroxy-tert-leucine (L-pantonine, 1c) was proposed as an intermediate in the biosynthesis of pantoic acid. 7 With an eye to the synthesis of highly biologically active, cyclic peptides, we sought to fulfill a need for a general synthesis of highly-β-branched α-amino acids.Racemic syntheses of tert-alkyl-α-amino acids have been reported. 8 Asymmetric preparation of L-1a and L-1b was achieved by tandem-enzyme coupled reductive amination of the tmolinski@ucsd.edu.

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Polydiscamide A: a new bioactive depsipeptide from the marine sponge Discodermia sp

Cited by 72 publications

References 0 publications

Lithistid Sponges: Star Performers or Hosts to the Stars

Lithistid Sponges: Star Performers or Hosts to the Stars

Natural Proline-Rich Cyclopolypeptides from Marine Organisms: Chemistry, Synthetic Methodologies and Biological Status

Diastereoselective Allylstannane Additions to (S)-5,6-Dihydro-2H-5-phenyloxazin-2-one. A Concise Synthesis of (S)-β-Methylisoleucine

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