Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr₄/PPh₃ and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior

• Christian Schumacher,
• Jas S. Ward,
• Kari Rissanen,
• Carsten Bolm and
• Mohamed Ramadan El Sayed Aly

Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9

• butter provide the body with its daily needs of cholesterol. In addition, hepatocyctes synthesize cholesterol through the mevalonate pathway. Dietary cholesterol is absorbed into the blood stream through a specific membrane bound protein named Niemann-Pick C1-Like 1 (NPC1L1) on the gastrointestinal tract

Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d₂)

• Petri A. Turhanen

Beilstein J. Org. Chem. 2022, 18, 1466–1470, doi:10.3762/bjoc.18.153

• diester (ApppI(d2)) is described. ApppI has been reported to be an important mevalonate pathway metabolite, induced by nitrogen-containing bisphosphonates used for the treatment of several diseases related to the calcium metabolism, of which osteoporosis is the most well-known. The availability of ApppI

• spectrometry. Keywords: ApppI; ATP; deuterium labelling; HPCCC; mevalonate pathway; NMR; synthesis; Introduction It has become clear and evident that phosphonate chemistry plays a crucial role in drug research and development [1][2][3][4]. There are several phosphonate-containing compounds under research or

• prevent protein isoprenylation by inhibiting farnesyl pyrophosphate synthase in the mevalonate pathway. This process leads to the formation of a series of compounds of which the structures have been reported elsewhere [10][11][12][13]. In 2006, Mönkkönen et al. have reported that the use of NBPs led to

Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves

• Christin Walther,
• Pamela Baumann,
• Katrin Luck,
• Beate Rothe,
• Peter H. W. Biedermann,
• Jonathan Gershenzon,
• Tobias G. Köllner and
• Sybille B. Unsicker

Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118

• by the mevalonate pathway in fungi [42]. The condensation of DMAPP with varying numbers of IPP residues results in products of various chain lengths: geranyl diphosphate (GPP, C10), farnesyl diphosphate (FPP, C15), and geranylgeranyl diphosphate (GGPP, C20). Terpene synthases (TPS) then convert the

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• isoprenoid precursors are synthesized via the mevalonate pathway (MVA) starting from acetyl-CoA [26]. Alternatively, in the majority of eubacteria, cyanobacteria, green algae and in the plastids of plants isoprenoid biosynthesis originates from glyceraldehyde-3-phosphate (G3P) and pyruvate [26][27

Synthesis of medronic acid monoesters and their purification by high-performance countercurrent chromatography or by hydroxyapatite

• Elina Puljula,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2016, 12, 2145–2149, doi:10.3762/bjoc.12.204

• the mevalonate pathway [6]. In addition, IPP is known to be able to stimulate gamma delta (γδ) T-cells [7] and BP monoesters have been demonstrated to exert effects on γδ T-cells as well [8][9]. Activators of γδ T-cells have been claimed to be potentially useful for cancer immunotherapy [10

Recent highlights in biosynthesis research using stable isotopes

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

• acetyl nucleophile at the growing chain. This mechanism is similar to the formation of hydroxymethylglutaryl-CoA along the mevalonate pathway in isoprenoid biosynthesis [22]. Recently, a different additional mechanism of β-branching was reported, in which a special PKS module is catalyzing the reaction

Two strategies for the synthesis of the biologically important ATP analogue ApppI, at a multi-milligram scale

• Janne Weisell,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2015, 11, 2189–2193, doi:10.3762/bjoc.11.237

• -methylbut-3-enyl)triphosphoric acid diester] (1) are described. ApppI is an active metabolite of the mevalonate pathway and thus is of major biological significance. Chemically synthezised ApppI was purified by using triethylammonium bicarbonate as the counter ion in ion-pair chromatography and

• groups have different mechanisms of action in the body. N-BPs, such as alendronate, inhibit the mevalonate pathway (MVP) in cells and promote the formation of ApppI, which has been demonstrated to induce apoptosis in osteoclasts [3]. Furthermore, ApppI has the ability to activate T cells together with

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• regulation of the biosynthesis of phenazine natural products. In a previous study, we described the biosynthetic gene cluster for prenylated phenazines from Streptomyces anulatus (Figure 1) [11]. This cluster contained the seven core phenazine biosynthesis genes, the mevalonate pathway genes and a

• prenyltransferase gene ppzP and, downstream thereof, the genes of the mevalonate pathway for supply of the isoprenoid precursor dimethylallyl diphosphate (DMAPP). Upstream of ppzP, four genes, orf1-orf4, could be identified. Database comparisons by using BLAST and Pfam searches gave no obvious clues as to whether

• the center of the endophenazine cluster In between the mevalonate pathway genes and the dihydro-PCA biosynthesis genes, four further genes are situated, i.e., ppzTUVM (Figure 1). The gene ppzM (1023 bp) shows similarities to PhzM from Pseudomonas aeruginosa PAO1, a putative phenazine-specific