Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• recent studies [9][10][11][12][13][14]. Most of them belong to the adenylate-forming enzyme superfamily (ANL superfamily) and utilize ATP to activate nitrous acid by AMPylation, with the only exception being AzpL in alazopeptin biosynthesis, which is a membrane protein that catalyzes diazotization

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• model enzymes for PPK1 and PPK2 [9][10]. From a structure perspective, PPK1 enzymes form tetramers in solution with a mass of approximately 80 kDa for the monomer (Figure 2b). Although not being an integral membrane protein, the enzyme is described to be membrane-associated [11][12][13]. The phosphate

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• further expanded the applications of n-FABS into the screening and direct IC50 measurement of bioactive substrates within intact living cells [45]. By studying mammalian cells expressing the membrane protein fatty acid amide hydrolase (FAAH), they showed that it is possible to screen and identify target

Encrypting messages with artificial bacterial receptors

• Pragati Kishore Prasad,
• Naama Lahav-Mankovski,
• Leila Motiei and
• David Margulies

Beilstein J. Org. Chem. 2020, 16, 2749–2756, doi:10.3762/bjoc.16.225

• receptors is described. We show that the binding of DNA-based artificial receptors to E. coli expressing His-tagged outer membrane protein C (His-OmpC) induces a Förster resonance energy transfer (FRET) between the dyes, which results in the generation of a unique fluorescence fingerprint. Because the

• reversibly change the properties of the cell. For example, we have shown that synthetic receptors appended with a thiol or a folate group enable bacteria expressing the His-tagged outer membrane protein C (His-OmpC) to bind to gold surfaces or cancer cells, respectively [2]. We have also shown that this

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• ) [1][2][3][4][5][6][7][8]. Interestingly, MPD is synthesized on the cytoplasmic face of the ER and must be translocated across the ER membrane to participate in luminal glycosyltransfer reactions [3][4]. A specific membrane protein – MPD scramblase – is required to facilitate the transbilayer movement

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• , especially in therapeutic proteins and peptide-based vaccines [18]. Enhanced catabolic stability [6] can arise from the role of particular aromatic amino acids in membrane–protein interactions [19]. Furthermore, fluorinated aromatic amino acids can alter enzymatic activity as a result of enhanced protein

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• Comparing the activities of biohybrid catalysts based on the small β-barrel proteins NB and Sav with the large membrane protein FhuA reveals striking differences. Interestingly, much higher activities were observed when the catalysts were incorporated into the cavities of small β-barrel proteins. For the

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

• Rebeka Jójárt,
• Szabolcs Pécsy,
• György Keglevich,
• Mihály Szécsi,
• Réka Rigó,
• Csilla Özvegy-Laczka,
• Gábor Kecskeméti and
• Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

• and Economics, H-1521 Budapest, Hungary 1st Department of Medicine, University of Szeged, Korányi fasor 8–10, H-6720 Szeged, Hungary Membrane protein research group, Institute of Enzymology, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok körútja 2, H-1117 Budapest

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• nor did the silencing of (N)-WASP by RNA interference alter the suppression of secretory and membrane protein production by mycolactone. The angiotensin pathway was identified as a third target of mycolactones by Brodin and co-workers in 2014 [104]. It has been known for some time that mycolactone is

2-Methyl-2,4-pentanediol (MPD) boosts as detergent-substitute the performance of ß-barrel hybrid catalyst for phenylacetylene polymerization

• Julia Kinzel,
• Daniel F. Sauer,
• Marco Bocola,
• Marcus Arlt,
• Tayebeh Mirzaei Garakani,
• Andreas Thiel,
• Klaus Beckerle,
• Tino Polen,
• Jun Okuda and
• Ulrich Schwaneberg

Beilstein J. Org. Chem. 2017, 13, 1498–1506, doi:10.3762/bjoc.13.148

• membrane protein solubilization, but is leading to protein unfolding as a drawback. Disadvantageous of detergents is the tremendous reduction of selectivity due to denaturing the protein or the reduction of productivity by detergent micelles since hydrophobic compounds are most likely located inside the

• demonstrate the importance of the right choice of the membrane protein stabilizer for biohybrid catalysis. Results and Discussion For solubilizing the transmembrane protein FhuA ΔCVFtev PE–PEG and MPD were applied as stabilizing agent and phenylacetylene polymerization was performed as model reaction (Figure

• selectivity [13]. The membrane protein FhuA ΔCVFtev in MPD shows stability for more than three days under the reaction conditions and therefore is leading to significantly increased yields. Conclusion In conclusion, we successfully demonstrated the use of MPD as small-molecule stabilizer for utilization of

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• maintaining the membrane’s barrier function by increasing the bilayer packing density through condensing the phospholipids. Furthermore, cholesterol is an important player in the dynamic domain structure of the plasma membrane and the formation of lateral lipid domains with relevance to membrane protein

Artificial Diels–Alderase based on the transmembrane protein FhuA

• Hassan Osseili,
• Daniel F. Sauer,
• Klaus Beckerle,
• Marcus Arlt,
• Tomoki Himiyama,
• Tino Polen,
• Akira Onoda,
• Ulrich Schwaneberg,
• Takashi Hayashi and
• Jun Okuda

Beilstein J. Org. Chem. 2016, 12, 1314–1321, doi:10.3762/bjoc.12.124

• : artificial Diels-Alderase; biohybrid catalysis; copper enyzme; membrane protein; Introduction So-called artificial metalloenzymes have attracted attention over the last decade [1][2][3][4][5][6][7][8][9]. Incorporation of an organometallic cofactor into proteins offers new possibilities to expand the

• hydroxamate uptake protein component A (FhuA) as host for defined Cu(I) NHC or Cu(II) terpyridyl complexes with a maleimide moiety. By covalently bonding these copper complexes to the protein artificial Diels–Alderases based on a membrane protein have been obtained. Results and Discussion Synthesis of the

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• natural products. These uridine-derived nucleoside-peptide antibiotics inhibit the bacterial membrane protein translocase I (MraY), a key enzyme in the intracellular part of peptidoglycan biosynthesis. This review describes the structures of naturally occurring muraymycins, their mode of action, synthetic

• and was used in assays mentioned above as a crude cellular membrane preparation or as a detergent-solubilised membrane protein mixture [79][84]. A purification to homogeneity was reported for MraY from B. subtilis by Bouhss et al. in 2004 [81] and for the congener from Aquifex aeolicus by Lee et al

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• electrochemistry [18] or by adding an oxidizing agent [19]. Different studies have employed this concept to form redox-responsive systems applied, for example, in self-healing materials [19], polymeric hydrogels [20][21], voltage-responsive vesicles [22], ultrasentive enzyme sensors [23], and as a plasma membrane

• protein isolation method [24]. So far, this concept has not been applied to SNPs. Here, we aim to make SNPs with a redox-switchable assembly/disassembly mechanism. As a proof of concept, we used positively charged CD-grafted poly(ethylene imine) (CD-PEI) as a host, positively charged ferrocene-terminated

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• environment of the cell can result in the differentiation of two DC subsets identified by the expression level of the CD1 membrane protein referred to as CD1a+ and CD1a− cells [31]. The continuous survey of the intracellular compartments of DCs is an important step in handling both protein and lipid antigens

• effect of the n−3 PUFAs was also demonstrated by the decreased expression of CD1a membrane protein in the cell surface, the decreased secretion of the pro-inflammatory cytokine IL-6 and the PUFA-mediated modulation of GPR120 receptor expression dependent on the mode of moDC activation. The treatment of

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• products, to biomedical applications including MRI imaging agents [1][2][3], membrane-protein crystallisation media [4][5][6] and solubilising bioactive food additives (Figure 1) [7]. Furthermore, recent research has centred on the use of amphiphile nanoparticles for drug-delivery applications [8][9][10

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• TARDBP, which encodes for the trans-activating response (TAR) DNA-binding protein 43 (TDP-43), FUS/TLS, which encodes the RNA-binding protein fused in sarcoma, and VAPB, a gene encoding the vesicle-associated membrane-protein-associated protein B/C, and animal models based on mutations in these genes

Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes

• Tony Taldone,
• Anna Rodina,
• Erica M. DaGama Gomes,
• Matthew Riolo,
• Hardik J. Patel,
• Raul Alonso-Sabadell,
• Danuta Zatorska,
• Maulik R. Patel,
• Sarah Kishinevsky and
• Gabriela Chiosis

Beilstein J. Org. Chem. 2013, 9, 544–556, doi:10.3762/bjoc.9.60

• saponin can be used to reversibly open cellular pores and allow antibody entry, thus allowing for retention of cell viability, if this is desired [25]. Staining with CD45, a plasma membrane protein, was used as a positive control for detection of cell-surface Hsp90 (Figure 3a and b). The contribution to

• fluorescence intensity. CD45 is a plasma-membrane protein. For microscopy, nuclei were stained with DAPI. (a) and (b) right panels; quantification of repeat experiments (n = 2). Reagents and conditions: (a) D-biotin, DCC, DMAP, CH2Cl2, sonicate; (b) EZ-Link® NHS-LC-Biotin, DIEA, DMF, 35 °C or rt; (c) EZ-Link