Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• compounds allowing for the preparation of porphyrins with different reactive groups such as hydroxy and amino derivatives capable for further functionalization and conjugation of these porphyrins to other substrates. In addition, conjugates containing maleimide or biotin entities in the structure of

• has become one of the most popular route for the site-selective modification of cysteine residues in bioconjugation technology. We suppose that the maleimide group in porphyrin 11 is a useful target for thiol conjugation via Michael addition reactions [44]. This also concerns biotin-conjugated organic

• molecules which have been also used for selective delivery of the drug to cancer cells [45]. Here, biotin was conjugated to porphyrin 12 which was obtained by alkylation of the amino group in compound 5 with chloroacetyl chloride (10) to give porphyrin biotin conjugate 14 in 76% yield (Scheme 4). We also

Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells

• Fumihiro Ishikawa,
• Sho Konno,
• Hideaki Kakeya and
• Genzoh Tanabe

Beilstein J. Org. Chem. 2024, 20, 445–451, doi:10.3762/bjoc.20.39

• introduced a pegylated biotin linker at the 2′-OH group of ʟ-Phe-AMS and confirmed that the probe retains the binding activities toward the A-domain of GrsA, a gramicidin S synthetase. Aldrich et al. developed a Sal-AMS-based activity-based probe (ABP) to profile MbtA in M. tuberculosis [12]. In contrast, we

• us to measure the dissociation constant (Kd) of the test compounds (Figure S1a, Supporting Information File 1). The ʟ-Phe-AMS-biotin probe was immobilized on a streptavidin-coated 96-well plate and incubated with recombinant His6-tagged GrsA in the presence or absence of inhibitors (Figure S1b

• , Supporting Information File 1). After washing, the wells were incubated with an anti-His6 tag antibody and subsequently with a horseradish peroxidase-conjugated secondary antibody. The amount of GrsA bound to ʟ-Phe-AMS-biotin was determined by measuring the absorbance of o-phenylenediamine dihydrochloride at

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

• Jon Lundstrøm,
• Emilie Gillon,
• Valérie Chazalet,
• Nicole Kerekes,
• Antonio Di Maio,
• Ten Feizi,
• Yan Liu,
• Annabelle Varrot and
• Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

• lipid-linked glycans. Then the detecting solution composed of anti-polyHistidine (Sigma-Aldrich, Merck, SAB4200620) and biotin anti-mouse IgG (Sigma-Aldrich, Merck, B7264) antibodies (10 µg/mL, precomplexed in a ratio of 1:1) was overlaid onto the arrays for 1 h. The final detection was with a 30 min

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• extraction of Nocardia altamirensis For siderophore production, the strain was grown in 5-L Erlenmeyer flasks containing 1 L of iron-free M9 medium: 7.52 g/L Na2HPO4×2H2O, 3.0 g/L KH2PO4, 0.5 g/L NaCl, 0.5 g/L NH4Cl, 4 g/L glucose, 0.247 g/L MgSO4×7H2O, 0.074 g CaCl2×2H2O, 1 mL biotin (1 mg/mL), 1 mL

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation

• Jennifer Frommer and
• Sabine Müller

Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234

• , assays that implement separation steps require RNA molecules conjugated to an affinity tag such as biotin, or any other functionality for functional selection [11][12]. Very importantly, terminal modification/functionalization is not always suitable to a specific aim. Thus, in addition to building blocks

Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides

• Rémi Martinent,
• Javier López-Andarias,
• Dimitri Moreau,
• Yangyang Cheng,
• Naomi Sakai and
• Stefan Matile

Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167

• efficient delivery of a model protein (avidin, around 67 kDa) into cells through biotin–avidin technology could be achieved in the presence of this strikingly small peptide. However, the uptake of peptide 9-labeled avidin was dramatically reduced into cells that express less GAGs on the cell surfaces. These

• added to minimize the passive diffusion across the membrane and to maximize the solubility in water. Biotin was used to interface the transporter and streptavidin to probe the COC-mediated protein delivery. A chloroalkane, finally, was needed for the HC CAPA. The trifunctional transporter 23 was first

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

• moiety for photocrosslinking to MPD-recognizing proteins. The presence of an additional propargyl group provides a way to further derivatize the probe with biotin azide via click-type chemistry [16] for the isolation of protein–lipid adducts using streptavidin resins [10]. To synthesize such molecular

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

• Grzegorz Mlostoń,
• Mateusz Kowalczyk,
• André U. Augustin,
• Peter G. Jones and
• Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

• thioketones; sulfur heterocycles; tetrahydrothiophenes; Introduction Functionalized tetrahydrothiophenes constitute an important group of five-membered sulfur heterocycles; many of them, both chiral and achiral, with biotin as the best-known representative, form the key motif in numerous compounds of great

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF₃SO₃H. NMR and DFT studies of dicationic electrophilic species

• Dmitry S. Ryabukhin,
• Alexey N. Turdakov,
• Natalia S. Soldatova,
• Mikhail O. Kompanets,
• Alexander Yu. Ivanov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1962–1973, doi:10.3762/bjoc.15.191

• common motif present in some components of human organisms, histidine, vitamin B12, purines, histamine, biotin, and in natural compounds such as lepidiline A and B [6]. Over the years of active research, benzimidazole derivatives have been involved in medicinal chemistry covering a wide range of

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• urea groups can participate in intermolecular hydrogen bonding resulting in the formation of tubular [5][6][7] or gel-like [8] structures. Ureas lacking of N–H hydrogen atoms such as ethyleneureas, glycolurils, and biotin are also important building blocks of macrocyclic receptors such as cucurbiturils

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• (e.g., biotin) [64]. Importantly, the effective implementation of on-resin Ugi-4CRs paved the way for the subsequent development of multicomponent macrocyclizations permitting the introduction of PEGs, sugars and fluorescent labels at resin-linked peptides [66][67]. More recently, Wessjohann and Rivera

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

• Jessica Hassenrück and
• Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

• were incubated with Tz-biotin, followed by incubation with streptavidin-AlexaFluor 555 (strep-AF555) for visualization (Scheme 1). In confocal fluorescence microscopy experiments, all sugars showed a distinct cell membrane staining in comparison to the negative control (Figure 3A). As expected [25][27

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• supramolecular, dative, as well as covalent anchoring. Ward and co-workers reported the first artificial metathase based on the biotin–(strept)avidin technology in 2011 [65], thus expanding the set of reported reactions with this class of ArMs [66]. It is well known that the biotin–(strept)avidin couple

• olefin-bearing biotin 84 was selected as olefinic partner for the CM reaction with the modified antibody, yielding IgG-Fc-Ahc32-biotin (Scheme 19b). The conjugated protein can be selectively pulled-down with avidin beads and analyzed by tandem MS after tryptic digestion. This strategy suggests that CM

• tags. c) PEG-tethered catalysts. Chemical structure and components of amphiphilic molecule PTS and derivatives. In vivo metathesis with an artificial metalloenzyme based on the biotin–streptavidin technology. Most common metathesis reactions. Ring-opening metathesis polymerization (ROMP), acyclic diene

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

• are supramolecular, dative and covalent anchoring. Supramolecular anchoring was pioneered by Wilson and Whitesides in 1978 [27]. They made use of the high affinity of (strept)avidin (Sav) to biotin that represents one of the strongest supramolecular interactions found in nature with a dissociation

• synthesized by Ward [29]. A GH-type second generation olefin metathesis catalyst was modified at the periphery of an NHC ligand with a biotin moiety [46]. The small β-barrel protein avidin (Avi) or streptavidin (Sav) was incubated with the catalyst to give the artificial metalloprotein. This (strept)avidin

• cavity. During this study, already a hint at the importance of the spacer length became apparent. A short spacer between the GH-type catalyst (Ru-1) and the biotin moiety did not lead to a successful conversion of the substrate. Elongation of the spacer (Ru-2) and therefore moving the active site

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• culture was inoculated into 100 mL of the IMM-HS production medium (glucose 1%, K2HPO4 0.36%, KH2PO4 0.41%, MgSO4·7H2O 0.02%, CaCl2·2H2O 0.01%, FeSO4·7H2O 0.002%, NH4Cl 0.1%, biotin 0.0001%, and L-histidine 0.4%), and shaken at 200 rpm at 30 °C for 4 days. For the extraction of secondary metabolites, 100

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

• Françoise Debart,
• Christelle Dupouy and
• Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

• activation induces the release of photoresponsive moieties during photoirradiation, yielding a lower extent of GFP expression in HeLa cells [72]. Later, Mc Master showed that it is not necessary to heavily modify siRNA because a single photoresponsive unit (biotin linked to nitrophenylethyl, Figure 4) at the

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

• Lingjun Xu,
• Shuwen Han,
• Linjie Yan,
• Haifeng Wang,
• Haihui Peng and
• Fener Chen

Beilstein J. Org. Chem. 2018, 14, 309–317, doi:10.3762/bjoc.14.19

• great utility of chloramphenicol base scaffold in industrial production of enantiopure compounds is the synthesis of a precursor of biotin (vitamin H) by the chloramphenicol base-promoted asymmetric methanolysis of meso-cyclic anhydrides [41][42][43]. Despite extensive studies on chloramphenicol-base

Fluorogenic PNA probes

• Tirayut Vilaivan

Beilstein J. Org. Chem. 2018, 14, 253–281, doi:10.3762/bjoc.14.17

• binding domain and the stem part consisted of a chimeric PNA–DNA hybrid linked together by a disulfide bond (Figure 4). The chimeric beacon was immobilized to a microtiter plate via a biotin tag and was employed for the detection of PCR amplicons of rDNA from Entamoeba histolytica [41]. The use of PNA

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• elegant solution consisted in the application of glucose attached at position 6’ via a glutaryl group as a long-chain hydrophilic linker in combination with biotin or the hydrophilic fluorescent label AlexaFluor. The appropriately protected tetraacylated disaccharide 19 was subjected to treatment with Zn

• pyrophosphate to furnish exclusively α-configured fully protected glycosyl phosphotriester. Global deprotection by catalytic hydrogenolysis over Pd-black gave E. coli lipid A functionalized with the glutaryl-Glc linker 23 which served as a key precursor for the preparation of fluorescent- or biotin-labeled

• compounds using labeling reagents having a hydrazide group. A hydrophilic fluorescence group Alexa Fluor 568 and polyethylene glycol-linked biotin were introduced using hydrazone formation reaction between the aldehyde group of the glutaryl-Glc linker and the hydrazide group of the labeling reagent. In

Synthetic mRNA capping

• Fabian Muttach,
• Nils Muthmann and
• Andrea Rentmeister

Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274

• with a 6-thioguanosine cap analogue. Synthesis of biotin-labeled caps was achieved with a 2′-NH2-modified cap analogue which was reacted with an N-hydroxysuccinimide biotin active ester [73]. The biotin-labeled cap analogue could be incorporated into mRNA during IVT and retained binding to eIF4E and

• dyes which could be applied as FRET pair. In this case, labeling was achieved in two bioorthogonal reactions, an iEDDA and a SPAAC reaction. Furthermore, dual modification with an azido and an alkyne function enabled fluorophore/biotin labeling using a combination of SPAAC and CuAAC reaction. Efficient

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

• ) [120] rescued L929 fibroblasts from mycolactone-promoted apoptosis while silencing FoxO3 by RNA interference was only partially protective. The latter finding might be explained by the compensating effects of other FoxO proteins. Two synthetic mycolactone-derived probes bearing a biotin tag as a

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• corresponding monomers, appended to Ir bipyridine complexes, oligoethylene glycol and biotin entities, have been examined by fluorescence spectroscopy for their self-assembling behavior and biodetection capability (Scheme 15). In a very interesting work, Blechert, Buchmeiser and coworkers [61] copolymerized

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• a solution containing the other split aptamer fragment functionalized with a biotin. In the first step of the assay, the concentration of the target molecule is transduced into a dose-dependent ligation of the split aptamer, which then allows for pull-down of a streptavidin-functionalized reporter

Biocatalysis for the application of CO₂ as a chemical feedstock

• Apostolos Alissandratos and
• Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

• number of carboxylases, phosphoanhydride bonds in ATP are hydrolysed to drive CO2 transformation through various molecular mechanisms. For example, biotin carboxylase catalysed reactions proceed through electrophilic activation of CO2 to carboxyphosphate to facilitate an attack by a nucleophile [28]. In