Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• a cooperative effect [94], which means that albumin binding significantly increases until an appropriate fatty acid chain length is reached. In 1998, seven binding sites of this multifunctional transport protein were identified by Curry et al. using X-ray crystallographic studies [95]. Later on

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

Site-selective covalent functionalization at interior carbon atoms and on the rim of circumtrindene, a C₃₆H₁₂ open geodesic polyarene

• Hee Yeon Cho,
• Ronald B. M. Ansems and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2014, 10, 956–968, doi:10.3762/bjoc.10.94

• explored immediately following the discovery of methods for bulk preparation of fullerenes in 1990 [28]. Within the first few years, several covalent functionalization sequences were introduced that became widely used for the construction of multifunctional architectures with C60 as an integral building

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

• Łukasz Górecki,
• Artur Mucha and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

• with trimethylamine oxide [31]. As the oxide also released the borane–quinuclidine complex at elevated temperature the free alcohol was obtained in a satisfactory yield. This alcohol was subjected to Swern oxidation, recommended for multifunctional compounds [32], to produce the target aldehyde 8 in 65

Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

• Jacques Lalevée,
• Sofia Telitel,
• Pu Xiao,
• Marc Lepeltier,
• Frédéric Dumur,
• Fabrice Morlet-Savary,
• Didier Gigmes and
• Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

• ][52][53][54][55]) in formulations containing multifunctional synthetic epoxides, acrylates, monomers/oligomers or epoxide/acrylate blends (renewable raw or modified materials are usable to some extent) with lights extending from the UV to the red, using polychromatic or monochromatic light sources

• ) [66]. All these reactions allowed the radical photopolymerization of formulations containing multifunctional synthetic acrylates using UV to red lights delivered by low intensity sources. A new PIC based on a panchromatic iridium complex and the associated performance in the photopolymerization area

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• additional functional groups on them by replacing the starting materials by activated alkenes and aldehydes. Various multifunctional molecules including natural products have already been successfully synthesized using the Baylis–Hillman adducts [9]. Structural features of grandiamide D, gigantamide A

Stereoselectively fluorinated N-heterocycles: a brief survey

• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

• . Instead, we will focus on two recent developments in deoxyfluorination methods that are particularly relevant to N-heterocyclic targets. Late stage deoxyfluorination is an attractive method for synthesising multifunctional fluorinated N-heterocycles, but mild and selective reagents are required if this is

• . Fluorinated miglitol analogues, and their inhibitory activity towards yeast α-glycosidase. Analogues of isofagomine (31) have different pKaH values, and therefore exhibit maximal β-glucosidase inhibition at different pH values. Late stage deoxyfluorination in the synthesis of multifunctional N-heterocycles

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• -delivery; hydrogel; multifunctional; nanofibers; NSAID; self-assembly; supramolecular; topical use; Introduction This article reports the design, synthesis, and characterization of hydrogelators made of non-steroidal anti-inflammatory drugs (NSAID) and small peptides for the development of multifunctional

New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators

• Sofia Telitel,
• Frédéric Dumur,
• Thomas Faury,
• Bernadette Graff,
• Mohamad-Ali Tehfe,
• Didier Gigmes,
• Jean-Pierre Fouassier and
• Jacques Lalevée

Beilstein J. Org. Chem. 2013, 9, 877–890, doi:10.3762/bjoc.9.101

• irradiation, we have recently started the search for suitable multifunctional arrangements exhibiting a strong coupling of the molecular orbitals MOs [42][43]. Improved absorption properties (red-shifted λ, higher ε) while keeping a high reactivity have been already achieved. Examples of these investigated

Thermotropic and lyotropic behaviour of new liquid-crystalline materials with different hydrophilic groups: synthesis and mesomorphic properties

• Alexej Bubnov,
• Miroslav Kašpar,
• Věra Hamplová,
• Ute Dawin and
• Frank Giesselmann

Beilstein J. Org. Chem. 2013, 9, 425–436, doi:10.3762/bjoc.9.45

• such as the organization of carbon nanotubes [17] or various nanoparticles [18] in a liquid-crystalline matrix. To reach the goal, several new multifunctional liquid-crystalline materials possessing either ethylene glycol units (denoted as TL1 and TL2) or a different number of hydroxy groups (denoted

• observed for the chiral compound in [26] having the same molecular core as TL4 but a branched chiral alkoxy chain instead of the decyloxy group used for TL4. The relation between the molecular structure and mesomorphic properties of these new multifunctional compounds with different structures is discussed

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

• -, oligonuclear and higher nuclearity complexes, polymeric 1D, 2D and 3D systems, 1D chain compounds and 2D and 3D networks, SCO in nanomaterials, and soft matter, such as metallomesogens, as examples for the main current objectives in SCO research, viz. synthesizing so-called multifunctional materials, which

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• mixtures are described in the literature [4], and dimers [5], trimers [6], and polymers have also been obtained [7]. A different approach is to synthesise cross-linked cyclodextrin-based polymers so as to prepare insoluble multifunctional cyclodextrin derivatives [8][9][10]. These polymers can be obtained

• used as excipients in preparing tablets, capsules, pellets, granules, suspensions, solid dispersions, or topical dosage forms or as new nanotechnological, multifunctional carriers [31][32]. In particular, the design of new nanodelivery systems to improve drug administration is currently being studied

• -fluorouracil and tamoxifen, as is shown in Table 1. Considering their versatility, nanosponges can act as multifunctional carriers, i.e., to enhance solubility, protect fragile molecules, and achieve sustained release. In many cases they act with two or more functions simultaneously. In this review we

Design and synthesis of quasi-diastereomeric molecules with unchanging central, regenerating axial and switchable helical chirality via cleavage and formation of Ni(II)–O and Ni(II)–N coordination bonds

• Vadim A. Soloshonok,
• José Luis Aceña,
• Hisanori Ueki and
• Jianlin Han

Beilstein J. Org. Chem. 2012, 8, 1920–1928, doi:10.3762/bjoc.8.223

• presence of two potentially reactive amide groups and the multifunctional nature of compounds 12. In particular, preparation of the most desirable NH-containing (R’ = H) derivatives 13, by reaction of 12 with ammonia or its derivatives, was not possible at all. Modification of the synthetic scheme with

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

• Ângelo M. L. Denadai,
• Frederico B. De Sousa,
• Joel J. Passos,
• Fernando C. Guatimosim,
• Kirla D. Barbosa,
• Ana E. Burgos,
• Fernando Castro de Oliveira,
• Jeann C. da Silva,
• Bernardo R. A. Neves,
• Nelcy D. S. Mohallem and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• modulated by selecting an appropriate organic molecule with desirable functional groups in its structure. In particular, magnetic organic–inorganic hybrid materials (MHMs) have attracted considerable attention based on their multifunctional and biocompatible properties [2][5][6]. Moreover, MHMs can present

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

• Chunhui Jiang,
• Fangrui Zhong and
• Yixin Lu

Beilstein J. Org. Chem. 2012, 8, 1279–1283, doi:10.3762/bjoc.8.144

• tryptophan based Trp-1 [46], as well as threonine incorporated multifunctional catalyst CD-3 [47]. However, no further improvement could be achieved (Table 1, entries 8–10). The influence of different imines on the reaction was subsequently explored, and it was found that the electronic nature of the

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• secretions of several alloxystine wasps [54] and their activity in intraspecific and interspecific communication has been discussed [55]. According to first bioassays, the new iridoids seem to play a multifunctional role in the tritrophic system of the aphid Sitobion avenae, its parasite, the wasp Aphidius

Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins

• Hang Zhang,
• Shan-Jun Zhang,
• Qing-Qing Zhou,
• Lin Dong and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2012, 8, 1241–1245, doi:10.3762/bjoc.8.139

• investigation of a Lewis base catalyzed asymmetric allylic amination of Morita–Baylis–Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high

• ][28], as outlined in Scheme 1. Thus, multifunctional chiral 3-amino-2-oxindoles could be obtained in a straightforward manner. Results and Discussion Based on the above considerations, we initially investigated the reaction of MBH carbonate 2a and a diversity of nucleophilic nitrogen sources by the

• electron-withdrawing groups exhibited a slower reaction rate, but both good yields and ee values were still obtained (Table 2, entries 5–10). As outlined in Scheme 2, some synthetic transformations were conducted with the multifunctional allylic amination product 4d. The N–O bond cleavage of 4d could be

Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman carbonates with maleimides

• Hong-Ping Deng,
• De Wang,
• Yin Wei and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 1098–1104, doi:10.3762/bjoc.8.121

• of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People’s Republic of China 10.3762/bjoc.8.121 Abstract We have developed a multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita–Baylis–Hillman

• previous literature. Keywords: asymmetric [3 + 2] annulation; maleimides; Morita–Baylis–Hillman carbonates; multifunctional thiourea-phosphine; organocatalysis; Introduction Highly functionalized cyclopentene derivatives are important subunits in a variety of biologically active molecules and have

• effective catalysts in the [3 + 2] annulation of MBH carbonates with isatylidene malononitriles to give the desired products in high yields with high enantioselectivities [50]. Furthermore, our group recently also synthesized a series of L-phenylalanine-derived multifunctional thiourea-phosphine catalysts

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

Synthetic approaches to multifunctional indenes

• Neus Mesquida,
• Sara López-Pérez,
• Immaculada Dinarès and
• Ermitas Alcalde

Beilstein J. Org. Chem. 2011, 7, 1739–1744, doi:10.3762/bjoc.7.204

• multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• of bacterial cell membranes can be tuned, e.g., by the introduction of methyl branches or olefinic double bonds [1]. The biosynthesis of FAs is a repetitive chain elongation process catalysed in animals and fungi by multifunctional megasynthases, and in plants or bacteria by a set of discrete enzymes

A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols

• Jie Li and
• Pengcheng Huang

Beilstein J. Org. Chem. 2011, 7, 426–431, doi:10.3762/bjoc.7.55

• required [22][23][24][25]. For example, multifunctional arylacetylenes 2i and 2k were prepared in 85% and 83% yields in 5 min (Table 3, entries 10 and 11), whereas they were obtained in only 38% and 11% yields in 8 h, respectively, when sodium was used in refluxing toluene (Supporting Information File 1

Tribenzotriquinacenes bearing three peripheral or bridgehead urea groups stretched into the 3-D space

• Jörg Tellenbröker and
• Dietmar Kuck

Beilstein J. Org. Chem. 2011, 7, 329–337, doi:10.3762/bjoc.7.43

• [1][2][3][4][7], the attachment of multifunctional groupings at the convex surface of the TBTQ skeleton has been only scarcely examined [4]. Therefore, we subjected the previously described bridgehead triaminotribenzotriquinacene 12 [4] to the reaction with phenylisocyanate in analogy to the

Hybrid biofunctional nanostructures as stimuli-responsive catalytic systems

• Gernot U. Marten,
• Thorsten Gelbrich and
• Annette M. Schmidt

Beilstein J. Org. Chem. 2010, 6, 922–931, doi:10.3762/bjoc.6.98

• of the superparamagnetic cores in combination with the thermoresponse of the shell. These multifunctional hybrid particles are formed by surface initiated copolymerization of oligo(ethylene glycol) methyl ether methacrylates (labeled as MEMA (M), MEEMA (M’) and OEGMA (O)) with N-succinimidyl

• . The principle described here is applicable to the modification of other biologically or catalytically relevant groups, and will therefore open new ways for the design of multifunctional hybrid nanostructures with different property portfolios. Experimental Materials: Ammonium hydroxide aqueous

• enzymatic digestion of BAPNA catalyzed by magnetically labeled trypsin (). Proposed mechanism of catalytic activity after heating magnetic biocatalyst particles above Tc. Physical and chemical composition of investigated multifunctional core–shell nanoparticles. Acknowledgements Thanks to Prof. T. J. J

Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s

• Richard Hoogenboom,
• Martin W. M. Fijten,
• Guido Kickelbick and
• Ulrich S. Schubert

Beilstein J. Org. Chem. 2010, 6, 773–783, doi:10.3762/bjoc.6.96

• of well-defined polymer architectures is of major importance for the development of complex functional materials. In this contribution, we discuss the synthesis of a range of multifunctional star-shaped tosylates as potential initiators for the living cationic ring-opening polymerization (CROP) of 2

• hydrophobic; and from hard materials, with a high glass transition temperature via crystalline and chiral polymers [7], to soft materials, with a very low glass transition temperature [8][9]. The synthesis of star-shaped poly(2-oxazoline)s has been reported using a range of multifunctional electrophilic

• -pEtOx (top). b) SEC traces of TetraTos-B and star-PEtOx (in CHCl3:NEt3:2-PrOH; UV-detector at 500 nm). SEC spectrum obtained for star-pEtOx utilizing a photodiode-array detector (eluent: DMF containing 5 mM NH4PF6). General reaction scheme for the preparation of multi-tosylates from multifunctional