Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• : decaprenyl-phosphate phosphoribosyltransferase, G7: chlorophyll synthase, and G8: homogentisate Ptases. AuaA is used as outgroup Ptase from Stigmatella aurantiaca. Regional alignment of ubiA-297 of Maribacter sp. MS6 (EU359911.1) and homologous genes in Z. uliginosa DSM 2061 (NZ_FTOB01000006), A

Evidence for an iterative module in chain elongation on the azalomycin polyketide synthase

• Hui Hong,
• Yuhui Sun,
• Yongjun Zhou,
• Emily Stephens,
• Markiyan Samborskyy and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2016, 12, 2164–2172, doi:10.3762/bjoc.12.206

• Stigmatella aurantiaca [20], further examples have been uncovered in the PKSs for aureothin [21][22], borrelidin [23][24], lankacidin [25][26], neoaureothin [27], etnangien [28], crocacin [29], ebelactone [30] and thiolactomycin [31][32]. Given the close mechanistic analogy between fatty acid synthases and an

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• been used against skin diseases due to its mutagenic effect [71]. Bacterial monobenzo-α-pyrones were isolated from the myxobacterium Stigmatella aurantiaca MYX-030. Myxocoumarins A (65) and B (66) were identified, and 65 was tested for antifungal activity [72]. It showed a promising activity against

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

• Tobias A. M. Gulder,
• Snežana Neff,
• Traugott Schüz,
• Tammo Winkler,
• René Gees and
• Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

• The myxobacterial strain Stigmatella aurantiaca MYX-030 was selected as promising source for the discovery of new biologically active natural products by our screening methodology. The isolation, structure elucidation and initial biological evaluation of the myxocoumarins derived from this strain are

• described in this work. These compounds comprise an unusual structural framework and exhibit remarkable antifungal properties. Keywords: antifungal activity; myxobacteria; natural products; Stigmatella aurantiaca; structure elucidation; Introduction Despite declining interest of most big R&D-driven

• percentage of antifungal myxobacterial natural products, we investigated the potential of new myxobacterial isolates towards the production of novel, agrochemically relevant antifungal lead structures. The results obtained with strain Stigmatella aurantiaca MYX-030 are described herein. Results and

A practical synthesis of long-chain iso-fatty acids (iso-C₁₂–C₁₉) and related natural products

• Mark B. Richardson and
• Spencer J. Williams

Beilstein J. Org. Chem. 2013, 9, 1807–1812, doi:10.3762/bjoc.9.210

• sources [1] including the myxobacterium Stigmatella aurantiaca [21][65], and the oral bacterium Veillonella parvula [66], although the absolute configuration has not been reported. Diastereoselective hydroxylation [67] of the chelated Z-enolate derived from 28 using the Davis oxaziridine [68] afforded the

Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues

• Xu-Wen Li,
• Jennifer Herrmann,
• Yi Zang,
• Philippe Grellier,
• Soizic Prado,
• Rolf Müller and
• Bastien Nay

Beilstein J. Org. Chem. 2013, 9, 1551–1558, doi:10.3762/bjoc.9.176

• cyclization. Keywords: antiplasmodial activities; Conrad–Limpach reaction; mitochondrial membrane potential; natural products; quinolones; total synthesis; Introduction The four aurachins A–D (1–4) were first isolated from the myxobacterium Stigmatella aurantiaca strain Sg a15 in 1987 (Figure 1) [1]. This

• yield of the natural product. Indeed from a culture batch of 60 L, the production of compound 4 by Stigmatella aurantiaca Sg a15 under basal conditions was described as less than 1 mg/L after about 6 days [1]. This production was improved by the addition of anthranilic acid (i.e., the aurachin

• under these experimental conditions, although the intermediate imine was supposedly formed during the reaction but not isolated. The carbocyclic core of aurachin H Aurachin H (6) was isolated from Stigmatella aurantiaca at the same time as the aurachin series A–L [3]. Biosynthetically, it may arise from

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• -methylundecan-2-one (34), has been reported from plants [43][44][45][46] and bacteria, e.g., from the myxobacterium Stigmatella aurantiaca and arctic bacteria of the cytophaga-flavobacterium-bacteroides group [47][48]. In some of these bacteria a pattern of methylketones similar to that of X. c. pv. vesicatoria

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• -methylpentanoate (5), methyl isocaproate (6), and methyl 3-methylpentanoate (7) were found in actinomycetes [11][12]. Methyl 9-methyldecanoate (8) is released by the myxobacterium Stigmatella aurantiaca DW4/3-1 [13]. A complex mixture of several methyl 2-methylalkanoates (9–26) was recently reported from the

• 8 was previously found in Stigmatella aurantiaca [13], whereas the compounds 102 and 103 (from leucine), and 98 (from valine) have not been described before. The same is true for all FAMEs described here that are derived from a branched amino acid and that are in addition α- or γ-methyl-branched