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Search for "metabolite" in Full Text gives 160 result(s) in Beilstein Journal of Organic Chemistry.
Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663
Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57
- endophenazine B as a minor product (Figure 1) [11]. In the present study, we carried out inactivation experiments of genes on cosmid ppzOS04, followed by heterologous expression of the modified clusters and chemical analysis of secondary metabolite formation. This allowed us to investigate the function of
- quantitative differences in production reliably. We decided to use cultivation in 24 square deep-well plates (EnzyScreen BV, The Netherlands). Previous studies have shown that this greatly reduces the variability of secondary metabolite production in comparison to cultivation in Erlenmeyer flasks [14]. In
- shown to increase the production of certain antibiotics [14]. Of each mutant obtained in this study, usually three independent clones were isolated, and secondary metabolite production was determined in three parallel cultivations for each clone. The variability of production between different clones
Aldol elaboration of 4,5,6,7-tetrahydroisoxazolo[4,3-c]pyridin-4-ones, masked precursors to acylpyridones
Beilstein J. Org. Chem. 2012, 8, 308–312, doi:10.3762/bjoc.8.33
- -tetrahydroisoxazolo[4,3-c]pyridin-4-one (8a) [19]. Ilicicolin H as an example of a 3-decalinoyl-4-hydroxypyridin-2-one metabolite. Aldol reactions of tetrahydroisoxazolopyridone 6. Reagents: (i) LDA–TMEDA, RCHO, THF, −20 °C; (ii) toluene, reflux, PTSA. Retrosynthetic analysis of a model 3-decalinyl-4,5,6,7
Conserved and species-specific oxylipin pathways in the wound-activated chemical defense of the noninvasive red alga Gracilaria chilensis and the invasive Gracilaria vermiculophylla
Beilstein J. Org. Chem. 2012, 8, 283–289, doi:10.3762/bjoc.8.30
- the up-regulated metabolites, arachidonic acid derived hydroxylated and dihydroxylated fatty acids are most prominent, with 7,8-dihydroxyeicosatetraenoic acid (7,8-di-HETE (3)) being the most active metabolite in the chemical defense against epiphytism. Recent work indicates that the invasive G
- an additional signal of an arachidonic acid derived metabolite with a characteristic UV spectrum of a conjugated tetraene. Purification yielded about 2.3 mg of an unstable metabolite, which was submitted to MS, 1D and 2D-NMR analysis. The molecular formula C20H28O2 was determined by HRMS–ESI ([M + Na
- ]+ calcd for 323.1986; found, 323.1982). 1H–1H COSY allowed us to follow the entire spin system of the metabolite, including 10 olefinic protons, 7 CH2, 1 CH3 and 1 CH groups (Scheme 1, spectra are shown in Supporting Information File 1). In combination with HMBC data all hydrogen and carbon signals were
Advances in synthetic approach to and antifungal activity of triazoles
Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79
- , and is excreted in an inactive form via liver and kidneys. Fluconazole is 94% absorbed and its oral bioavailability is not affected by food or gastric pH. It is excreted unchanged in urine with t1/2 = 25–30 h. Itraconazole is largely metabolized in liver by cytochrome P450 3A4, an active metabolite is
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57
- atorvastatin which has a five times greater potency then the initial lead, the fungal metabolite compactin (5, Figure 2). Although it was possible to construct such fully substituted pyrrole rings by ZnCl2-catalysed condensation reactions between a functionalised enamine 6 and simple benzoin (7), this method
Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer
Beilstein J. Org. Chem. 2010, 6, No. 8, doi:10.3762/bjoc.6.8
- and biologically active secondary metabolites [1]. (+)-Harzialactone A (1), a marine metabolite isolated from the culture broth of a strain of Trichoderma harzianum OUPS-N115 by Numata and co-workers, exhibited antitumor and cytotoxic activities against cultured P388 cells [2]. The absolute
Synthesis of phosphonate and phostone analogues of ribose-1-phosphates
Beilstein J. Org. Chem. 2009, 5, No. 37, doi:10.3762/bjoc.5.37
- phosphonate 8a was obtained (Figure 2) which confirmed its structure and stereochemical relationship to intermediate ribose-1-phosphate metabolite 5. Clearly, phosphonate 8a formed a 1:1 salt with the amine. Additionally, 23a and 22a were treated in separate reactions with acetic anhydride in dry pyridine [13
Mitomycins syntheses: a recent update
Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33
- unique activity was thought to originate from their ability to transform in vivo to generate the active metabolite. This was followed by decades of investigations to understand in detail their singular mode of action. It was found that the aziridine played a crucial role, allowing an irreversible bis
A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine
Beilstein J. Org. Chem. 2007, 3, No. 41, doi:10.1186/1860-5397-3-41
- toward DNA repair-deficient yeast mutants;[7] azaspiracids are marine phycotoxins isolated from cultivated mussels in Killary harbor, Ireland;[8] and chlorofusin A is a novel fungal metabolite showing the potential as a lead in cancer therapy.[9] In addition, aza-spiropyrans C, being able to equilibrate
Multiple hydride reduction pathways in isoflavonoids
Beilstein J. Org. Chem. 2006, 2, No. 16, doi:10.1186/1860-5397-2-16
- of isoflavones [10][16][17][18][19][20]. Deoxybenzoins (5) and propenols (6) Isoflavanones undergo a facile retro-Michael-type ring opening [21][55] under basic conditions to give the propenone intermediate 14 (Figure 2), sometimes considered [56] to be an independent isoflavone metabolite but
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