128425-11-6Relevant articles and documents
Ruckerbactin Produced by Yersinia ruckeri YRB Is a Diastereomer of the Siderophore Trivanchrobactin Produced by Vibrio campbellii DS40M4
Butler, Alison,Dulaney, Kalana,Reitz, Zachary L.,Stow, Parker R.,Thomsen, Emil
, p. 264 - 269 (2022/01/15)
The Gram-negative bacterium Yersinia ruckeri is the causative agent for enteric red mouth disease in salmonids. The genome of Y. ruckeri YRB contains a biosynthetic gene cluster encoding the biosynthesis of catechol siderophores that are diastereomeric with the known vanchrobactin class of siderophores, (DHBDArgLSer)(1–3). Ruckerbactin (1), produced by Y. ruckeri YRB, was found to be the linear tris-l-serine ester composed of l-arginine and 2,3-dihydroxybenzoic acid, (DHBLArgLSer)3. The biscatechol, (DHBLArgLSer)2 (2), and monocatechol, DHBLArgLSer (3), compounds were also isolated and characterized. The macrolactone of ruckerbactin was not detected. The presence of LArg in ruckerbactin makes it the diastereomer of trivanchrobactin with DArg. The electronic circular dichroism spectra of Fe(III)–ruckerbactin and Fe(III)–trivanchrobactin reveal the opposite enantiomeric configurations at the Fe(III) sites. Fe(III)–ruckerbactin adopts the Δ configuration, and Fe(III)–trivanchrobactin adopts the Λ configuration. Y. ruckeri YRB was also found to produce the antimicrobial agent holomycin (4).
Namalides B and C and Spumigins K-N from the Cultured Freshwater Cyanobacterium Sphaerospermopsis torques-reginae
Sanz, Miriam,Salinas, Roberto Kopke,Pinto, Ernani
, p. 2492 - 2501 (2017/09/27)
Chemical investigations of the terrestrial cyanobacterium Sphaerospermopsis torques-reginae ITEP-024 from northern Brazil afforded namalides B (1) and C (2), the first analogues of this anabaenopeptide-like metabolite to be described. Four other related peptides (3-6), termed spumigins K-N, were also identified. Planar structures and absolute configurations for 1, 2, and 3a-6a were deduced by a combination of 2D NMR, HRMS analysis, and Marfey's methodology. Spumigins K-N (3-6) are the first examples of spumigins containing a 2-hydroxy-4-(4-hydroxyphenyl)butanoic acid (Hhpba) in the N-terminal position. Compounds 1 and 2 inhibited carboxypeptidase A with IC50 values of 0.75 and 2.0 μM, respectively.
Eight micropeptins from a Microcystis spp. bloom collected from a fishpond near Kibbutz Lehavot HaBashan, Israel
Vegman, Margarita,Carmeli, Shmuel
, p. 10108 - 10115 (2013/11/06)
Eight new micropeptin-type cyclic depsipeptides, micropeptins LH920, LH1021, LH1048, LH1062, LH911A, LH911B, LH911C, and LH925, along with five known micropeptins, three known anabaenopeptins and two known microcystins (LR and RR), were isolated from a wa