Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

• Daniel I. Hădărugă,
• Mustafa Ünlüsayin,
• Alexandra T. Gruia,
• Cristina Birău (Mitroi),
• Gerlinde Rusu and
• Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

• –2.2 g/100 g of salmon [9][12]. The health benefit of omega-3 FAs (but especially EPA, (all-Z)-5,8,11,14,17-eicosapentaenoic acid and DHA, (all-Z)-docosa-4,7,10,13,16,19-hexaenoic acid) in reducing cardiovascular risk by reducing blood lipids (mainly LDL cholesterol and triglycerides), is well known

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• ]. Actually, the galactosylation of polymers or lipids has been utilized to develop drug carriers with hepatocyte specificity through ASGPR [11]. Therefore, ASGPR-mediated endocytosis seems to be a promising approach to deliver CyDs to hepatocytes for the treatment of hepatosplenomegaly in NPC disease

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• ) Regioselective enzymatic acylation of natural products. Natural products are traditionally classified into groups of substances (terpenes, alkaloids, amino acids, lipids, etc), depending on their biosynthetic origin and on their chemical and structural features [19][20][21]. The complex structures of most of

Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2015, 11, 913–929, doi:10.3762/bjoc.11.103

• between a LON and the lipids of the bilayer, which leads to a decrease in diffusion time. However, it is not clear if the diffusion slows down gradually. For this, it would be necessary to measure the diffusion at various positions above or below the bilayer. This is, however, difficult because of the

• -phosphoethanolamine (POPE) and 1-palmitoyl-2-oleyl-sn-glycero-3-phosphocholine (POPC) were purchased from Avanti Polar Lipids (Alabaster, Al), n-decane from Alfa Aesar (D-Karlsruhe), potassium chloride (KCl), 3-morpholinopropane-1-sulfonic acid (MOPS) and 2-amino-2-(hydroxymethyl)propane-1,3-diol (TRIS) were

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• building blocks to construct functional materials by means of biomolecules. Recent studies have made use of DNA, lipids, peptides, and proteins to build up organic–inorganic hybrid materials [9]. Due to their versatile and unique functionalities, which can be used for catalytic [13], optics [14], and

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• defensive low molecular weight thiol [7]. 2-C-acetamide and 2-C-acetonyl carbohydrate derivatives have also been reported to serve as inhibitors of the biosynthesis of lipids [8][9] and cell surface engineering [10], respectively. The main synthetic protocols for the synthesis of 2-C-branched sugars involve

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• activity and the ability to reduce the synthesis of hepatic lipids and of eicosanoids. It inhibits platelet aggregation and protects vessels from arteriosclerosis [34][35][36][37][38]. In recent years, it has been reported that resveratrol is sufficiently potent to inhibit VEGF-induced and FGF-2

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• relatively rigid molecular and supramolecular systems. These systems mainly consist of peptides and proteins (e.g., scleroproteins, globular proteins, and membrane proteins), lipids (e.g., biological membranes), carbohydrates (e.g., cellulose) and nucleic acids (DNA, RNA). The impressive performance of the

• hydrophobic backbone of the ARs and the markedly smaller surface of the FOL conformation. This behavior resembles folding of peptides and self-assembly of lipids. It is well known that cyclodextrines (CDs), bearing a hydrophobic cavity and a hydrophilic exterior, are able to encapsulate small hydrophobic

• be a versatile tool to investigate the STR/FOL equilibrium. We systematically investigated this phenomenon as a function of solvent viscosity, cyclodextrine addition and in the presence of lipids forming micelles and vesicles. In contrast to these noncovalent STR–FOL transitions we also reported on

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

• the effects of n−3 PUFAs was based on our previous results demonstrating that the development of human monocyte-derived DC (moDC) is highly sensitive to environmental cues among them the level and composition of lipids and fatty acids [30]. These studies also revealed the phenotypic and functional

• Solubilization of n−3 PUFAs Cyclodextrins (CDs) are efficient solubilizers of lipids [42]. The water-insoluble n−3 PUFAs were solubilized in aqueous solutions of randomly methylated α- and β-CD (RAMEA and RAMEB, respectively), but the similar γ-CD derivative, RAMEG was ineffective to modulate the solubility

• lipid rafts in the cell membrane. The complexation efficiency [43] calculated from the solubility data characterize the affinity of the various methylated CDs toward the lipids studied (Table 1). The complex association constants were not calculated because the intrinsic solubility in water is so low

Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase

• María Emilia Cano,
• Rosalía Agusti,
• Alejandro J. Cagnoni,
• María Florencia Tesoriero,
• José Kovensky,
• María Laura Uhrig and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324

• and 120 min gave very similar results (not shown). A steric effect operating on the sialylation of multiple Galp residues has been previously suggested for lactosyl lipids attached to membrane microdomains [40]. The dependence of the amount of disialylation of the divalent glycans on the concentration

A study on the inhibitory mechanism for cholesterol absorption by α-cyclodextrin administration

• Takahiro Furune,
• Naoko Ikuta,
• Yoshiyuki Ishida,
• Hinako Okamoto,
• Daisuke Nakata,
• Keiji Terao and
• Norihiro Sakamoto

Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300

• : Micelle formation of cholesterol with lecithin and bile salts is a key process for intestinal absorption of lipids. Some dietary fibers commonly used to reduce the lipid content in the body are thought to inhibit lipid absorption by binding to bile salts and decreasing the lipid solubility. Amongst these

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

Multivalent glycosystems for nanoscience

• Thisbe K. Lindhorst

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

• molecular shaping. They adopt more forms and shapes than one can conceive in 24 hours. They exist as small mono- or oligo-saccharides, as large and highly complex polysaccharides, and in conjugation with, for example, proteins and lipids, forming a kingdom of glycoconjugates that are found on every cell

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• -phosphoethanolamine (POPE) and 1-palmitoyl-2-oleyl-sn-glycero-3-phosphocholine (POPC) were purchased from Avanti Polar Lipids (Alabaster, Al), n-decane from Alfa Aesar (Karlsruhe, Germany), dimethyl sulfoxide (DMSO), potassium chloride (KCl), 3-morpholinopropane-1-sulfonic acid (MOPS) and 2-amino-2

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• ; metabolic oligosaccharide engineering; Introduction The glycan chains of glycoproteins and lipids have been shown to be involved in numerous biological recognition and regulation events [1]. Glycan research, especially the visualization of glycoconjugates in vitro and in vivo, has significantly profited

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

• Naoya Oku,
• Miyako Matsumoto,
• Kohsuke Yonejima,
• Keijiroh Tansei and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

• chrysogenum) revealed that all these layers varied in the extent of activity against certain test organism(s). Especially intriguing was the antifungal activity exhibited by the n-hexane-soluble fraction, which, in most cases, comprises lipids. To identify the responsible constituent, the fraction was

Photoswitchable precision glycooligomers and their lectin binding

• Daniela Ponader,
• Sinaida Igde,
• Marko Wehle,
• Katharina Märker,
• Mark Santer,
• David Bléger and
• Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

• affinity carbohydrate ligands by displaying several monosaccharides/oligosaccharides on a protein scaffold or through a patch of lipids. This is known as the glycocluster effect or the multivalent presentation of sugar ligands [3][4]. This strategy can also be employed for the synthesis of carbohydrate

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

• Ulrike Groenhagen,
• Michael Maczka,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

• polyketides, nonribosomal peptides, terpenoids, alkaloids, lipids and others. Such compounds became a major source of biologically active natural products as antibiotics, cytotoxic compounds, immunosuppressants etc. In addition, actinomycetes are also able to produce and release a wide variety of volatile

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

• Melanie Rauschenberg,
• Eva-Corrina Fritz,
• Christian Schulz,
• Tobias Kaufmann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

• and polymers offers a virtually unlimited number of encodings. In nature, carbohydrates are often linked to lipids, peptides or proteins. These conjugates are found inside cells, on cell membranes as well as in extracellular fluids and matrices. Surprisingly, the general understanding of the function

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

3-Pyridinols and 5-pyrimidinols: Tailor-made for use in synergistic radical-trapping co-antioxidant systems

• Luca Valgimigli,
• Daniele Bartolomei,
• Riccardo Amorati,
• Evan Haidasz,
• Jason J. Hanthorn,
• Susheel J. Nara,
• Johan Brinkhorst and
• Derek A. Pratt

Beilstein J. Org. Chem. 2013, 9, 2781–2792, doi:10.3762/bjoc.9.313

• antioxidant activities. The interplay of α-tocopherol and ascorbate (vitamin C) in preventing the oxidation of LDL lipids is perhaps the best-known example of such synergism, since the regeneration of α-tocopherol by reduction of the α-tocopheroxyl radical by ascorbate prevents TMP, and effectively turns a

Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

• John Li,
• May May Leong,
• Alastair Stewart and
• Mark A. Rizzacasa

Beilstein J. Org. Chem. 2013, 9, 2762–2766, doi:10.3762/bjoc.9.310

• evaluation of the resolvin series in preclinical models of bacterial sepsis has stimulated strong interest in their therapeutic potential, as RvD2 appears to express the unusual combination of anti-inflammatory and antimicrobial activity. Further interest in inflammation-resolving lipids is stimulated by

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

• Assaad Nasr El Dine,
• Ali Khalaf,
• Danielle Grée,
• Olivier Tasseau,
• Fares Fares,
• Nada Jaber,
• Philippe Lesot,
• Ali Hachem and
• René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

• to investigate the preparation and uses of new propargylic fluorides [12][13][14], which have been employed in the synthesis of fluorinated analogues of lipids [15][16] and in carbocyclic systems [17][18]. They have also been used for the preparation of several 5 and 6-membered heterocycles [19][20

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• -dimethylvaleronitrile) (MeO-AMVN), an azo initiator that decomposes at physiological temperatures 15 times faster than the corresponding AMVN, allowed the trans,cis conjugated hydroperoxides to be obtained exclusively and in good yields by direct oxygenation of the corresponding lipids. In fact, due to its ideal O–H

A peptidic hydrogel that may behave as a “Trojan Horse”

• Nicola Castellucci,
• Giorgio Sartor,
• Natalia Calonghi,
• Carola Parolin,
• Giuseppe Falini and
• Claudia Tomasini

Beilstein J. Org. Chem. 2013, 9, 417–424, doi:10.3762/bjoc.9.44

• this “Trojan Horse” strategy. Many peptides can penetrate mammalian cell membranes and take cargo with them. To enable penetration, initial binding of the peptide to the cell surface through electrostatic interactions with lipids, presumably followed by membrane destabilization to allow translocation