Depsipeptides strained cyclic

Rouhiainen L, Paulin L, Suomalainen S, Hyytiainen H, Buikema W, Haselkom R, Sivonen K (2000) Genes Encoding Synthetases of Cyclic Depsipeptides, Anabaenopeptilides, in Anahaena Strain 90. Mol Microbiol 37 156... 

Cyclosporins, produced by the filamentous fungus Tolypocladium niveum and by numerous strains of Fusaria and Neocosmospora, are a class of cyclic undecapep-tides which are composed of hydrophobic aliphatic amino acids [73-75], They exhibit antiinflammatory, immunosuppressive, antifungal, and antiparasitic properties [74], The main metabolite, cyclosporin A, is in clinical use worldwide under the trade name SANDIMMUN to prevent allograft rejection [77,78], Besides cyclosporin A, there are 24 naturally occuring cyclosporins which have substitutions of amino acids in positions 1, 2, 4, 5, 7, and 11 and/or contain unmethylated peptide bonds in positions 1,4,6,9,10, or 11 [79-82], Cyclosporin A contains three nonproteinogenic amino acids D-alanine in position 8, L-a-aminobutyric acid in position 2, and, in position 1, the unusual amino acid 4(R)-4-[(E)-2-butenyl]-4-methyl-L-threonine (Bmt) (Fig. 8). All three amino acids have to be synthesized by a pathway independent of the primary metabolism. In addition, several peptide bonds of the cyclosporin molecule are A -mcthylated similar to the depsipeptides enniatin, beauvericin and PF1022A-related peptides. 

N-Methylsansalvamide 11, a new cyclic depsipeptide, was isolated from extracts of a cultured marine fungus, strain CNL-619. The fungus was identified as a member of the genus Fusarium. Compound 11 exhibited weak in vitro cytotoxicity in the NCI human tumor cell line screen (GI50, 8.3 pM). Synthesis towards N-methylsansalvamide was reported. ... 

Enniatin family, cyclic depsipeptides produced by strains of Fusarium. Members are enniatin A, cyclo-(-D-Hiv-Me-Ile-)3, enniatin B, cyclo-(-D-Hiv-MeVal-)3, and enniatin C, cyclo-(-D-Hiv-MeLeu-)3, enniatin D, cyclo-(-D-Hiv-MeLeu-D-Hiv-MeVal-D-Hyv-MeVal-), enniatin E, cyclo-(-D-Hiv-MelLe-D-Hiv-MeLeu-D-Hiv-MeVal-), and enniatin F, cyclo-(-D-Hiv-MeLeu-MeIle-D-Hiv-Melle-) which all contain D-a-hydroxyisovaleric acid (o-Hiv) besides various L-methylamino acids. Enniatins act as ionophores to form complexes with K+ ions which allow their transport across membranes. 

A cyclic depsipeptide from a hepatotoxic strain of the marine cyanobacterium Nostoc sp. N. inhibits protein phosphatase-1 at high concentrations in vitro ... 

CYP163B3 (P450sky) from Streptomyces sp. Acta 2897 is involved in the biosynthesis of the cyclic depsipeptides skyllamycin A and B, with antibacterial, immunosuppressive, cytostatic, and antiparasitic properties [233], Skyllamycin A has been isolated from different Streptomyces strains and is a potent inhibitor of the platelet-derived growth factor (PDGF) signaling pathway that is involved in important processes such as cellular proliferation and migration [234, 235]. The structure of skyllamycin has an unusual a-hydroxylated glycine residue, an N-terminal cinnamoyl side chain, and three P-hydroxylated amino acids ((25, 55)-p-hydroxyphenylalanine,... 

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