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

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• be efficacious in the cellular delivery of oligonucleotides such as DNA [5][6][7] and RNA [8][9][10][11]. Conjugates of polyamines with aliphatic lipids or cholesterol yielding, i.e., dioctadecylaminoglycylspermine (DOGS, transfectam) are well established reagents for the transfection of DNA and

Design of a novel tryptophan-rich membrane-active antimicrobial peptide from the membrane-proximal region of the HIV glycoprotein, gp41

• Evan F. Haney,
• Leonard T. Nguyen,
• David J. Schibli and
• Hans J. Vogel

Beilstein J. Org. Chem. 2012, 8, 1172–1184, doi:10.3762/bjoc.8.130

• -proximal region of gp41, which is known to interact at the interfacial region of the viral membrane and adopts a helical structure in the presence of lipids. Three synthetic peptides were designed to increase the net positive charge and amphipathicity of this 19-residue peptide. Ultimately, the peptide

• large blue shifts in the presence of negatively charged lipid species, while only small blue shifts were seen with zwitterionic ePC:ePE LUVs. Gp41w-FKA displayed similar behaviour to gp41w-KA except that the blue shifts were not as pronounced for the negatively charged lipids and there was almost no

• chains burying into the membrane. This effect was most pronounced in the presence of anionic liposomes, but all of the mixtures resulted in strong decreases in the calculated Ksv values (Figure 3). The other two peptides, gp41w-KA and gp41w-FKA, demonstrate a preference for anionic lipids and detergents

Partial thioamide scan on the lipopeptaibiotic trichogin GA IV. Effects on folding and bioactivity

• Marta De Zotti,
• Barbara Biondi,
• Cristina Peggion,
• Matteo De Poli,
• Haleh Fathi,
• Simona Oancea,
• Claudio Toniolo and
• Fernando Formaggio

Beilstein J. Org. Chem. 2012, 8, 1161–1171, doi:10.3762/bjoc.8.129

• cycles of energy minimization by using a NOE force constant of 50 kcal/mol. The generated structures were visualized with the MOLMOL [74] (version 2K.2) program. Small unilamellar vesicles (SUVs) preparation DOPE and DOPG were purchased from Avanti Polar Lipids, Inc. (Alabaster, AL). The preparation of

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• - or oligosaccharides. The glycoprotein saccharides contribute physiochemical properties, influencing protein conformation or increasing stability against proteolytic activity. With their unique structural diversity and complexity, carbohydrates attached on proteins or lipids are involved in numerous

• mutant or a high-mannose oxazoline donor and an Endo-A mutant, two different homogenous glycoproteins 40 and 41 were formed (Scheme 7) [87]. Glycopeptide binding events Carbohydrates on proteins and lipids play critical roles in cell–cell and cell–external-agent binding events. Efforts in the preparation

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• C. albicans and F. neoformans. Saponins are known to be more effective against basidiomycetous yeast and at acidic pH act similarly to natural detergents, such as cellobiose lipids [27]. Growth inhibition experiments showed (Figure 6, Table 7), that the lower pH 4.0 favored antifungal activity of

Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR

• Michaela Braitsch,
• Hanspeter Kählig,
• Georg Kontaxis,
• Michael Fischer,
• Toshinari Kawada,
• Robert Konrat and
• Walther Schmid

Beilstein J. Org. Chem. 2012, 8, 448–455, doi:10.3762/bjoc.8.51

• membrane-bound (or attached) proteins, in which additional peaks originate from membrane lipids and raise severe technical problems. However, indirect detection techniques should always be cross-checked with reference experiments and suitable controls, to demonstrate selectivity of binding and to exclude

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

• for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). Keywords: actinomycetes; FAMEs; fatty acid biosynthesis; GC–MS; volatiles; Introduction Lipids in general, and particularly fatty acids (FAs), belong to the most

Planar-bilayer activities of linear oligoester bolaamphiphiles

• Jonathan K. W. Chui,
• Thomas M. Fyles and
• Horace Luong

Beilstein J. Org. Chem. 2011, 7, 1562–1569, doi:10.3762/bjoc.7.184

• underlying mechanism? One line of possibilities relates to the underlying “system property” mentioned earlier. It is known that pure lipids near their phase transitions can show single-channel conductance activities; while the specific mode of action depends on the identity of the lipid, discrete conductance

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• cell wall biosynthesis (e.g., thiacetazone, isoniazid, ethambutol, pyrazinamide, and ethionamide) with the cell wall of the tubercule bacillus being widely agreed as a promising target for new drugs [4][5]. The cell wall of all mycobacteria is especially rich in lipids and polysaccharides, with the

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• cross linking the diacetylene functional groups. Therefore, we have also synthesized and studied several diacetylene containing sugar lipids. Esterification of sugar headgroups with diacetylene containing long chain carboxylic acids can give the desired diacetylene containing lipids. Previously we had

• used headgroup 1 to synthesize a library of diacetylene containing lipids, and found that many of them are effective gelators [35]. Using the headgroup 8, we also synthesized six long chain diacetylene containing glycolipids 17A–17C and 18A–18C. We found that the diesters are effective gelators for

Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• ; glycoarrays; glycoconjugation; glycosylation; Introduction The chemical conjugation of carbohydrates through the anomeric centre to biomolecules such as peptides, proteins, lipids, metabolites and to array surfaces is an important synthetic challenge [1][2][3][4][5]. A diverse range of linkers and spacers

The development and evaluation of a continuous flow process for the lipase- mediated oxidation of alkenes

• Charlotte Wiles,
• Marcus J. Hammond and
• Paul Watts

Beilstein J. Org. Chem. 2009, 5, No. 27, doi:10.3762/bjoc.5.27

• of the esterases [13]. Changes in enzymatic behaviour observed when lipases are employed in organic solvent systems have led to their use in the synthesis of lipids, carbohydrate esters, amines and amides, along with finding industrial application in the synthesis of pharmaceuticals, fine chemicals

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

• Kirsti Parikka and
• Kristiina Wähälä

Beilstein J. Org. Chem. 2009, 5, No. 22, doi:10.3762/bjoc.5.22

• way for the immunochemical detection techniques of alkylresorcinols. Keywords: 5-n-alkylresorcinols; haptens; microwave assisted synthesis; Wittig reaction; Introduction 5-Alk(en)ylresorcinols and related compounds are phenolic lipids present in several families of plants (e.g. Gramineae

Stereoselective synthesis of (2S,3S,4Z)-4-fluoro- 1,3-dihydroxy- 2-(octadecanoylamino)octadec- 4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

• Gergana S. Nikolova and
• Günter Haufe

Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12

• configuration (2S,3S) of the products is controlled by the chiral auxiliary. In recent years several studies on cell membrane lipid models suggested that ceramide could act indirectly as a messenger by modulation of membrane properties. The membrane lipids (mostly sphingomyelin) together with cholesterol are

• networks, because its polar head groups can act both as acceptor and as a donor, ceramide, when added or generated in situ in the membrane, can segregate from the other lipids and cause coalescence of the small lipid raft domains to give highly ordered ceramide-enriched domains. Moreover, due to the small

Transition- metal/Lewis acid free synthesis of acyl benzothiophenes via C-C bond forming reaction

• Sarbani Pal,
• Mohammad Ashrafuddin Khan,
• P. Bindu and
• P. K. Dubey

Beilstein J. Org. Chem. 2007, 3, No. 35, doi:10.1186/1860-5397-3-35

• lipids while displaying potent estrogen antagonist properties in the breast and uterus. A most common example of SERM is tamoxifen which has been the therapy of choice in the endocrine treatment of all stages of hormone-dependent breast cancer and in the primary and secondary chemoprevention of breast