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Abstract

Peptide antibiotic with cyanolytic activity was isolated from the IGM52 strain of the Brevibacillus laterosporus Gram-positive spore-forming bacteria. By 1H NMR spectroscopy, this antibiotic was identified as loloatin A, a cyclic decapeptide cyclo(-Asn-Asp-Tyr-Val-Orn-Leu-DTyr-Pro-Phe-DPhe-). The spatial structure of loloatin A in solution was determined. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 4; see also http://www.maik.ru.

Solid‐Phase Synthesis of Macrocyclic Peptides via Side‐Chain Anchoring of the Ornithine δ‐Amine

“…To investigate the scope of the procedure three additional natural head‐to‐tail cyclic peptides that feature ornithine residues, namely tyrocidin A, loloatin A and streptocidin A, were synthesized in the same manner [2,48–50] . Tyrocidin A was obtained in a 66 % yield with a purity of 73 % (Entry 2).…”

“…To investigate the scope of the procedure three additional natural head-to-tail cyclic peptides that feature ornithine residues, namely tyrocidin A, loloatin A and streptocidin A, were synthesized in the same manner. [2,[48][49][50] Tyrocidin A was obtained in a 66 % yield with a purity of 73 % (Entry 2). In the synthesis of tyrocidin A, a concurrent cyclization and cleavage approach was employed by ösapay and co-workers using the Kaiser oxime resin furnishing tyrocidin A in a yield of 55 % with a > 95 % purity.…”

Complete Genome Sequence of Brevibacillus laterosporus Bl-zj, an Algicidal Bacterium Isolated from Soil

“…B. laterosporus was reported as a pathogen of invertebrates and an inhibitor of some bacteria and fungi, in which the extent of virulence was determined by the size and components of its spores and the specific extracellular metabolites (4–6). B. laterosporus strain Bl-zj was isolated from an intertidal zone soil sample in Zhanjiang, China (7), and was shown to have algicidal activity and to indirectly dissolve algae by secreting peptides (8).…”

Biologically active cyclic polypeptides with fragments of β-amino acid derivatives isolated from marine organisms (review)

“…The bacteria were first assigned to the Bacillus strain [53]. Later loloatin A was isolated from a strain of Gram-positive sporeforming bacteria Brevibacillus laterosporus [54]. Loloatins A-D possess in vitro activity against methycyclineresistant Staphylococcus aureus, vancomycin-resistant enterococcus, and drug-resistant Streptococcus pneumoniae [53], activity against cyanobacteria [54], and also activity against Gram-negative bacteria [55].…”

“…Later loloatin A was isolated from a strain of Gram-positive sporeforming bacteria Brevibacillus laterosporus [54]. Loloatins A-D possess in vitro activity against methycyclineresistant Staphylococcus aureus, vancomycin-resistant enterococcus, and drug-resistant Streptococcus pneumoniae [53], activity against cyanobacteria [54], and also activity against Gram-negative bacteria [55]. Koshikamide B (27), isolated from two different collections of the marine sponge Theonella sp., is a cyclopeptidolactone consisting of 17 amino acid residues: six proteinogenic amino acids, two D-isomers of proteinogenic amino acids, seven N-methylated amino acids, N(δ)-carbamoyl Asn, and 2-(3-amino-2-hydroxy-5-oxopyrrolidin-2-yl)propionic acid.…”