Multivalent glycosystems for nanoscience

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2014, 10, 2345–2347, doi:10.3762/bjoc.10.244

• nanoscience”. Bruce Turnbull (United Kingdom) has amassed contributions dedicated to “Synthetic methods to make multivalent glycosystems”, Alessandro Casnati (Italy) has delivered manuscripts regarding “Glycoconjugates for the delivery of drugs and diagnostic probes” for review, Roland Pieters (The

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

• Nattawut Yotapan,
• Chayan Charoenpakdee,
• Pawinee Wathanathavorn,
• Boonsong Ditmangklo,
• Hans-Achim Wagenknecht and
• Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

• shows several unique properties [26][27][28]. Its potential applications as a probe for DNA sensing are well-established. For example, we have developed singly labeled acpcPNA probes that can give a fluorescence change in response to hybridization to DNA [29][30][31]. Due to its solvatochromic

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• good affinity for Pseudomonas aeruginosa lectin lecA. They are convenient biological probes for investigating the roles of lecA and lecB in biofilm formation. Keywords: antibiotic; biofilm; glycocluster; lectin; multivalency effect; multivalent glycosystems; Introduction Pseudomonas aeruginosa (PA

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• ][9], anti-infective agents [10][11][12], or molecular probes [13][14]. Taking into account the importance of nucleoside analogs in medicine and biotechnology, there is a considerable interest in the development of simple and efficient synthesis of these compounds. Multicomponent reactions (MCRs

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• 7, 14183, Huddinge, Sweden 10.3762/bjoc.10.154 Abstract Pyrene derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, peptide nucleic acids (PNAs) containing 1 to 3 1-pyreneacetic acid units (PNA1–6) with a

• recognition; triplex stabilization; Introduction Peptide nucleic acid (PNA) probes are very selective in the recognition of DNA and have been used in a large variety of diagnostic methods, easily allowing the detection of point mutations at very low concentrations [1][2][3]. Poly-pyrimidine PNA can form very

• the fluorescence properties can be observed upon interaction with DNA, thus enabling to study the occurring interactions and to produce switching PNA probes. Fluorescent switching probes for DNA detection are very useful tools in diagnostics applications such as real-time PCR and in situ hybridisation

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• (Immunotech) directed against the following antigens (the tags are given in parentheses): CD80 (FITC), CD86 (PE), HLA-DR (ECD), CD83 (PC5). Cell vitality was tested with propidium iodide (PI, molecular probes). The cells were labelled in PBS with 1% FCS for 15 min at room temperature (rt), washed twice and

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

• Michał Górny vel Górniak,
• Anna Czernicka,
• Piotr Młynarz,
• Waldemar Balcerzak and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 741–745, doi:10.3762/bjoc.10.68

• Screening of the activity of large libraries of fluorogenic substrates of chosen enzymes is an emerging approach to determine their substrate preferences and thus to provide a set of data useful for the preparation of their selective inhibitors [1][2][3][4][5]. Such fluorogenic probes have been also used

• for profiling the proteolytic secretomes with the obtained profiles being useful as diagnostic tools [6][7][8]. Also conjugates of drugs with fluorescent probes have been used as so called theranostics (combination of therapeutics and diagnostics) [9][10]. Diaryl esters of α-aminoalkanephosphonic

• carrying fluorescent probes in their side chains or in the ester phosphonate moieties might find an application in constructing fluorescent probes for studying structural requirements of enzymes having serine in their active sites (proteinases and phosphatases) or to study their elevated level in various

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• natural product classes to inspire the synthesis of probes and reagents for chemical biology and medicinal chemistry research, we aimed at the development of a synthetic strategy to get access to the B-seco limonoid scaffold by means of a [3,3]-sigmatropic rearrangement as key step enabling the formation

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1–DNA-complex formation

• Midori A. Arai,
• Kyoko Uchida,
• Samir K. Sadhu,
• Firoj Ahmed and
• Masami Ishibashi

Beilstein J. Org. Chem. 2014, 10, 134–140, doi:10.3762/bjoc.10.10

• Education and Research (Development of SPECT Probes for Pharmaceutical Innovation) from MEXT and the Iodine Research Project in the Chiba University, the Asian Core Program (JSPS), Takeda Science Foundation, Hayashi Memorial Foundation for Female Natural Scientists, the Naito Foundation and the Tokyo

Flow microreactor synthesis in organo-fluorine chemistry

• Hideki Amii,
• Aiichiro Nagaki and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2013, 9, 2793–2802, doi:10.3762/bjoc.9.314

• production of PET agents with automation and ease of in-line purification is suitable for hospital use. To date, continuous flow microreactor technology has shown potential for synthesis of [18F]-radiolabeled molecular imaging probes such as [18F]FDG, [18F]fallypride, [18F]annexin, and so on, which were made

• [18F]-radiolabeled molecular imaging probes. Flow microreactor synthesis of dipeptides. Flow synthesis involving SNAr reactions. Flow synthesis of fluoroquinolone antibiotics. Highly controlled formation of PFPMgBr. Selective flow synthesis of photochromic diarylethenes. Flow microreactor system for

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

• Raoni S. B. Gonçalves,
• Michael Dos Santos,
• Guillaume Bernadat,
• Danièle Bonnet-Delpon and
• Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

• inhibitors [17][18][19][20][21]. Another powerful area, yet a somewhat less utilised role for fluorine is as a tag for 19F NMR that offers several analytical advantages including speed, sensitivity and selectivity [22][23]. Fluorinated molecules have served as valuable 19F NMR probes in high-throughput

Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification

• Akula Raghunadh,
• Satish S More,
• T. Krishna Chaitanya,
• Yadla Sateesh Kumar,
• Suresh Babu Meruva,
• L. Vaikunta Rao and
• U. K. Syam Kumar

Beilstein J. Org. Chem. 2013, 9, 2129–2136, doi:10.3762/bjoc.9.250

• research probes. The development of synthetic routes to these structures is often challenging. Chiral building blocks with three carbon atoms such as glycidol, 1-bromo-2,3-dihydroxypropane and 3-amino-1,2-dihydroxypropane (1) are considered powerful tools by synthetic chemists in organic synthesis [1][2][3

Temperature measurements with two different IR sensors in a continuous-flow microwave heated system

• Jonas Rydfjord,
• Fredrik Svensson,
• Magnus Fagrell,
• Jonas Sävmarker,
• Måns Thulin and
• Mats Larhed

Beilstein J. Org. Chem. 2013, 9, 2079–2087, doi:10.3762/bjoc.9.244

• ][15][16]. In contrast, microwave transparent fiber optic probes can be used for correct temperature measurements. In a recent tutorial review Kappe highlighted the difficulties of temperature monitoring under microwave heating [16]. We recently described the concept of a nonresonant microwave

• quite sensitive to rough handling and may break, and, according to our experience, fiber optic probes are generally susceptible towards higher temperatures at elevated pressures in organic solvents. Considering the above points the option of using the fiber optic probe as the standard tool for

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

• Matthew B. Plutschack,
• D. Tyler McQuade,
• Giulio Valenti and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 2022–2027, doi:10.3762/bjoc.9.238

• the pancreatic islets and hepatic cells of people with diabetes, which may explain glucose insensitivity and the progression of non-alcoholic fatty liver disease [6][7]. Passive carbohydrate transporters are well-known targets for carbohydrate-based probes [8]. The positron emission tomography (PET

• fewer tissues [2]. We are developing probes that are selectively transported by Glut5. Using design principles gleaned from the Holman group [13][14][15] as well as other fructose analogue research [16], we synthesized NBDM [17] and demonstrated that this probe is transported into cancer cells known to

• overexpress Glut5 and poorly transported into cells known to express little Glut5 [2][5][18]. We demonstrated that the transport is inhibited by fructose but not by other dietary sugars (glucose, glucosamine) [17]. Furthering our understanding of fluorescent probes like NBDM will expedite the development of

Synthesis of mucin-type O-glycan probes as aminopropyl glycosides

• David Benito-Alifonso,
• Rachel A. Jones,
• Anh-Tuan Tran,
• Hannah Woodward,
• Nichola Smith and
• M. Carmen Galan

Beilstein J. Org. Chem. 2013, 9, 1867–1872, doi:10.3762/bjoc.9.218

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• chemistry and drug discovery as biosensing probes, in immunoassays and in host–guest chemistry [71]. Ferrocene-substituted amino acids have been of significant importance in the investigation of the secondary structures of different peptides and foldamers [72]. Thus, conjugates of the azido-functionalized β

An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles

• Alexandre Jean,
• Jérôme Blanchet,
• Jacques Rouden,
• Jacques Maddaluno and
• Michaël De Paolis

Beilstein J. Org. Chem. 2013, 9, 1480–1486, doi:10.3762/bjoc.9.168

• presents an ideal push–pull configuration tunable with the pH by protonation of the pyridine ring. This is likely to lead to applications of 10a such as for new water-soluble molecular probes. Conclusion A new catalytic and regioselective preparation of substituted N-arylpyrroles decorated with various 2

Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways

• Eietsu Hasegawa,
• Minami Tateyama,
• Ryosuke Nagumo,
• Eiji Tayama and
• Hajime Iwamoto

Beilstein J. Org. Chem. 2013, 9, 1397–1406, doi:10.3762/bjoc.9.156

• reactions of substrates that contain appropriate probe moieties (Scheme 2). In past studies, we developed unique families of substances (exemplified by probes I and II in Figure 1) that act as radical ion probes [20] and found that radical intermediates in their reaction pathways undergo efficient 5-exo

• State University, USA) for his suggestion on radical ion probes. We also thank Mr. Junichi Sakai (Niigata University) for his assistance in making HRMS (EI) measurements.

True and masked three-coordinate T-shaped platinum(II) intermediates

• Manuel A. Ortuño,
• Salvador Conejero and
• Agustí Lledós

Beilstein J. Org. Chem. 2013, 9, 1352–1382, doi:10.3762/bjoc.9.153

• sensitive probes for coordinatively unsaturated Pt(II) complexes NMR spectroscopy has provided additional evidence for the existence of low electron-count Pt(II) complexes not only through the observation (in some cases) of NMR signals for the C–H bonds involved in agostic interactions, but also by the

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

• Laura Bekere,
• David Gachet,
• Vladimir Lokshin,
• Wladimir Marine and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2013, 9, 1311–1318, doi:10.3762/bjoc.9.147

• to be efficient fluorescent molecular probes [7][8]. Recently, the potential of amino-1,8-naphthalimides as fluorescent sensors in living cells has been reviewed [9]. Dendrimers involving the amino-1,8-naphthalimide moieties were showed to be promising active nondoping emitters [10]. 4-Amino

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• efforts to develop chemical probes to detect pathophysiological hallmarks of AD, such as amyloid-β plaques, for diagnosis and monitoring of therapeutic efficacy. This review provides a survey of chemical probes developed to date for AD with emphasis on synthetic methodologies and structure–activity

• relationships with regards to affinity for target and brain kinetics. Several probes discussed herein show particularly promising results and will be of immense value moving forward in the fight against AD. Keywords: Alzheimer’s disease; in vivo detection; near-infrared fluorescence probes; PET/SPECT imaging

• ; radioactive probes; Introduction Alzheimer’s disease (AD) is a progressive neurodegenerative disorder of the central nervous system currently affecting ~5.4 million Americans, a number that could increase to 11–16 million by the year 2050. In the United States, AD represents the 6th leading cause of death

Use of 3-[¹⁸F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

• Reik Löser,
• Steffen Fischer,
• Achim Hiller,
• Martin Köckerling,
• Uta Funke,
• Aurélie Maisonial,
• Peter Brust and
• Jörg Steinbach

Beilstein J. Org. Chem. 2013, 9, 1002–1011, doi:10.3762/bjoc.9.115

• remote imaging detectors, for both research and diagnostic purposes has considerably increased over the recent years. The success of this interdisciplinary field depends substantially on the development of molecular probes equipped with appropriate reporter groups [1]. Among the different imaging

• prosthetic groups were suggested and developed [5][6]. Their careful individual selection is critical for radiotracer development as they often exert great influence on target binding and/or stability in vivo. This is particularly valid when PET imaging probes based on small molecules are considered

Design and synthesis of tag-free photoprobes for the identification of the molecular target for CCG-1423, a novel inhibitor of the Rho/MKL1/SRF signaling pathway

• Jessica L. Bell,
• Andrew J. Haak,
• Susan M. Wade,
• Yihan Sun,
• Richard R. Neubig and
• Scott D. Larsen

Beilstein J. Org. Chem. 2013, 9, 966–973, doi:10.3762/bjoc.9.111

• and fibrosis. The molecular target for these compounds is unknown. To facilitate its identification, a series of tag-free photoaffinity probes was designed and synthesized, each one containing a photoactivatable group and an acetylenic end group for subsequent attachment to a fluorescent tag using

• ), which was less potent (IC50 9.8 µM versus 1.5 µM), but maintained similar maximal efficacy to that of 1 with significantly less cytotoxicity [8]. We therefore selected 2 as a template for the design of affinity probes. The successful isolation/identification of molecular targets for low-affinity ligands

• current hypothesis regarding the mechanism of action of 1 (redistribution of MKL primarily into the cytosol), which may require an intact actin cytoskeleton or nucleus. We thus elected to design photoaffinity probes that were tag-free, i.e., lacking either a biotin or fluorescent tag [17]. There are a

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• [2H6]DMSP and DMTeP as synthetic probes to study DMSP degradation pathways in marine bacteria The volatiles released by agar-plate cultures of Phaeobacter gallaeciensis DSM 17395 and Ruegeria pomeroyi DSS-3 strains grown on half-strength MB2216 medium supplemented with [2H6]DMSP or DMTeP were collected