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Search for "lipids" in Full Text gives 98 result(s) in Beilstein Journal of Organic Chemistry.
Photocatalyzed elaboration of antibody-based bioconjugates
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
- ) that can form covalent bonds when exposed to UV or visible light. These photoaffinity tags or crosslinkers are designed to bind to specific biomolecules, such as proteins, nucleic acids, or lipids, in a highly selective manner. The light irradiation triggers a chemical reaction, such as a bond
The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation
Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27
- , usually proteins or lipids by the process of glycosylation producing glycoproteins or glycolipids, respectively. Nature executes these processes by enzymatic pathways [18] and is often flawless in its desired output. But the scarcity and the cumbersome purification of natural enzymes limit the use of
Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies
Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261
- biomolecules like DNA and lipids. Lipid peroxidation and membrane disruption can cause random cross-linking, resulting in cell death and the fragmentation of proteins and enzymes. Elevated concentrations of reactive oxygen species (ROS) from various molecular processes contribute to the oxidation of proteins
- , nucleic acids, polysaccharides, and lipids. These modifications can impact the structure and biological functions of these molecules, ultimately leading to neuronal death, as observed in conditions like AD [30][31]. Recent studies highlight OS as an early event in AD pathogenesis, and mitochondria
Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions
Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231
- -size membrane (Croda International Plc. Avanti Polar Lipids, Inc.). Differential scanning calorimetry (DSC) DSC was performed using a MicroCalTMPEAQ-DSC System (Malvern Panalytical, Ltd., Malvern, U.K.). Liposomal suspensions of DMPC with or without catC60 or C60 were dispersed in PBS(–) (1 mM DMPC
The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis
Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222
- species. These glands can contain various lipids and peptides, but very often also complex mixtures of carboxylic acids. We report here the occurrence of novel methyl-branched unsaturated acids found in the secretions of six captive individuals living in a zoo. The structures of these compounds, 4.6
- (see, e.g., [1][2]). Comparative analysis of SGS through GC–MS has revealed an assortment of lipids (reviewed in [2]), such as cholesterol [3][4][5][6][7][8], carboxylic acids [4][5][7][8][9][10][11][12], alcohols [8], 1-O-monoalkylglycerols [6][8], and others [13]. Nitrogen-containing compounds
- , including piperidone [10], amines [5][10], and amides [3][5][10] have been also observed in certain species. The analyses of SGS in vipers (Viperidae) focused on New World pit vipers (Crotalinae). Early analyses of SGS lipids by thin-layer chromatography (TLC) [14], indicated that two pit vipers, the Timber
Computational toolbox for the analysis of protein–glycan interactions
Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180
- determinants that govern specific molecular interactions. Keywords: computational tools; glycan–protein interactions; MD; molecular recognition; Review Introduction Carbohydrates also referred to as saccharides, sugars, or glycans, constitute one of the main building blocks of biomolecules, alongside lipids
- , proteins, and nucleic acids. In humans and animals, they form the so-called glycocalyx, a protecting sugar coat decorating the cell surface and modulating a myriad of cell–cell interactions [1]. It is composed of branched or elongated glycan chains covalently linked to proteins or lipids, hereby
- interface, and a wide range of analysis tools for studying complex biomolecular systems. AMBER provides various force fields, specifically optimised for simulating biological molecules, as lipids (lipids21) [57], proteins (ff14SB) [58], water molecules (TIP3P) [59], general organic molecules (gaff2) [60
Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies
Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176
- on their own and in mixed micelles with lipids, on irradiation with either UV or blue light [21][22]. In addition, Ober et al. showed that in-situ UV irradiation stimulates a steady decrease in bilayer thickness for vesicles formed using Azo-modified phosphatidylcholine lipids, due to the shorter
- lipid tail length in the Z isomer [26]. Notably, these authors observed that the X-rays themselves also induced Z–E isomerisation in Azo-lipids, which they attributed to the X-ray radiolysis of water, which produces radicals and reactive species that can catalyse Z–E conversion [27]. This effect was
Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384
Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174
- many marine natural products [6][7], pyrroles substituted with long hydrocarbon chains (pyrrole lipids) are seldomly isolated, and their presence is limited to certain marine organisms [8]. A series of 3-alkylpyrrole-2-carbaldehydes/carboxylic acid/methylcarboxylate was reported from the marine sponge
Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors
Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46
- the release of fatty acids from the plastids to the endoplasmic reticulum, where they are utilized for the synthesis of acyl lipids that are essential components for various physiological and defensive processes [3][4][5][6]. As this enzyme target does not exist in other kingdoms, structure–activity
Switchable molecular tweezers: design and applications
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
- arms, can encapsulate planar aromatic molecules, making this system promising for drug delivery. The advancement of pH-switchable molecular tweezers laid the groundwork for the development of switchable lipids [20]. When such lipids are incorporated in lipid vesicles, they provide means for controlled
- release of siRNA or miRNA encapsulated within them into the solution in vitro and in vivo [21]. The closed conformation of 2 with parallel alkyl chains acts as a building block of the bilayer membrane and is packed together with other lipids. When the surrounding medium becomes acidic, the tweezers adopt
Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration
Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115
- %, and 100% CHOL). It is relevant to note that the percentage of CHOL in the formulations represents the amount of CHOL added to the fixed amount of DPPC not the sum of the total lipids. Thus, a formulation of 100% CHOL comprises a number of moles of CHOL equal to that of DPPC. These formulations were
- towards membrane lipids, the CD–phospholipid molar ratio, and the CHOL content in the membrane. Experimental Materials and methods Materials α-CD, β-CD, γ-CD, and randomly methylated-β-CD (RAMEB, DS = 12.9), were provided by Wacker Chemie (Germany). Low methylated-β-CD (CRYSMEB, DS = 4.9) and
- (Avanti Polar Lipids, Switzerland) of decreasing pore sizes resulting in a homogenous mixture of LUVs (large unilamellar vesicles). Finally, the purification of the SRB-loaded LUVs to eliminate unencapsulated SRB and lipid molecules from liposomes was carried out via a centrifugation (2 hours, 15 000 rpm
Synthesis of ether lipids: natural compounds and analogues
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
- Marco Antonio G. B. Gomes Alicia Bauduin Chloe Le Roux Romain Fouinneteau Wilfried Berthe Mathieu Berchel Helene Couthon Paul-Alain Jaffres Univ. Brest, CNRS, CEMCA UMR 6521, 6 Avenue Victor Le Gorgeu, 29238 Brest, France 10.3762/bjoc.19.96 Abstract Ether lipids are compounds present in many
- living organisms including humans that feature an ether bond linkage at the sn-1 position of the glycerol. This class of lipids features singular structural roles and biological functions. Alkyl ether lipids and alkenyl ether lipids (also identified as plasmalogens) correspond to the two sub-classes of
- naturally occurring ether lipids. In 1979 the discovery of the structure of the platelet-activating factor (PAF) that belongs to the alkyl ether class of lipids increased the interest in these bioactive lipids and further promoted the synthesis of non-natural ether lipids that was initiated in the late 60’s
Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87
- molecules that attack and destroy lipids and protein membranes of weed cells [10]. Fipronil is an inhibitor of GABA receptors and affects the nervous system of insects as a broad-spectrum insecticide [11][12]. On the other hand, thioamides are an important class of organic compounds. 6-Thioguanine and
Cyclodextrins as building blocks for new materials
Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66
- and lipids from viruses and envelopes and provide virucidal and bactericidal activity against a wide range of microorganisms [10]. Altogether, these findings highlight the ability of CDs to act as potential active pharmaceutical ingredients, which may influence the current regulatory framework for the
Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis
Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30
- oils was reported to further increase the oxidation stability and retardation of odor [15]. Poultry lipids have high contents of mono- and polyunsaturated FA glycerides, especially oleic and linoleic acid glycerides. The stability of chicken lipids was significantly increased by β-CD complexation which
- File 1, Figures S1–S4 and Tables S1 and S2). This means that a significant amount of β-CD is not involved in the formation of complexes and remains as β-CD hydrate in the mixture. These observations are in agreement with other studies on the complexation of vegetable (common bean lipids) and fish oil
1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures
Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12
- (hetero)aromatic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counterparts, but they do offer attractive transformations that can find good use in the assembly of a wide array of complex molecular architectures, ranging from lipids
Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B
Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185
- hydrophilic biological environments. Repeated studies on the bioactivity of lipopeptides have shown that the primary mechanism of action of these peptides involves interactions with the double layer of lipids and proteins that constitute the cell membrane [24][25][26]. This mechanism of action is important
Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity
Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72
- % pairwise identity) displayed similarities to geranylgeranylglyceryl phosphate synthases (EC 2.5.1.42), which are involved in the formation of polar membrane lipids of archaea and other bacteria [20], while group G4 contained close homologs of the protoheme IX farnesyltransferase (EC 2.5.1.141) (23–100
Menadione: a platform and a target to valuable compounds synthesis
Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43
- (DNA and RNA), enzymes, structural proteins, and cell membrane lipids. These effects can lead to dysfunctions that activate the apoptosis process resulting in cell death [42][43][44][45][46]. In addition to participating in redox cycles as biomolecules in various biochemical processes, the 1,4
1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis
Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5
- cause several damages to its components, such as carbohydrates, lipids, membrane components, and enzymes that are critical for DNA replication [9][10][11][12]. Most synthetic strategies toward naphthoquinones with potential biological activity start from natural and synthetic naphthoquinones, inserting
Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications
Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116
Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides
Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75
- lipid, 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC), cholesterol, and PEG-lipid, each with an essential role in the design (Figure 1). These lipids promote the effective distribution of the LNP in vivo as well as aid in effective cargo release from the endosome [1][37]. To this end, we herein
- mixture of DLin-MC3-DMA, DSPC, cholesterol, and 1,2-dimyristoyl-rac-glycero-3-methoxypolyethylene glycol-2000 (DMG-PEG 2000). Lipids were first extruded and then complexed with negatively charged aptamers annealed with fluorescently tagged complementary DNA oligonucleotides (GP160:A-1 or CCR5:G-3) to
- through stimulating the retinoic acid-inducible gene 1 (RIG-1) pathway, and it may thus be prudent to assess type-I interferons (IFN-α and IFN-β) in the future [32][59]. Importantly, the LNP B9 formulation alone had no effect on cell viability, suggesting that the ratio of cationic and ionizable lipids is
Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting
Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45
- occurrence of side reactions due to reactive groups introduced during PEG to lipids (or peptides) connecting reactions [23][24][25]. In particular, the PEG layer grafted on the surface of certain nanocarriers restricts the exposure of functional peptides [26][27]. Novel ligand-grafted lipids have been
- step by washing. The human epidermal growth factor receptor-2 (HER2)-targeting KCCYSL peptide–(SG)n–lipids in which the (SG)n (n = 3, 5, 7) sequence was used as a spacer allowed the reduction of the steric hindrance when compared to the conventional PEG2000 spacer [28]. Liposomes containing these
- peptide ligands dramatically increased cellular association in HER2-positive cells. Other lipids grafted to the RGD peptide and SG spacer were integrated in PEGylated liposomes and were efficiently associated with integrin αvβ3-expressing Colon-26 cells [25]. One of our general objectives is to synthesize
Selected peptide-based fluorescent probes for biological applications
Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247
- important biomolecules including nucleotides, DNA, proteins, lipids etc. in aqueous media. Fluorescent peptides have also been used for specific organelles such as lysosomes tracking. In this review, it is summarized Schmuck group’s tremendous effort in developing fluorescent peptide-based probes for
- for the turn on fluorescent detection of LPS in mixed solvent (DMSO/TBS buffer, 1:4) (Figure 10A) [59]. The liposomes are created by mixing two lipids in a ratio of 9:1. First lipid 12 is designed by attaching 10,12-tricosadiyonic acid to a penta-lysine oligopeptide bearing an aminonaphthalimide
Easy access to a carbohydrate-based template for stimuli-responsive surfactants
Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229
- surfactants are triggered, thereby releasing the cargo [8]. Guo and co-workers have earlier succeeded with the use of pH-sensitive surfactants and even introduced the term “flipids” for such pH-responsive lipids [7][8]. This term could also describe compounds where the binding of a guest molecule is able to
- -responsive lipids [11]. The three compounds reluctance to adopt a 1C4 conformation may be due to a steric clash between the methylene group at C5 and the anomeric substituent when both of these groups are in axial orientation. To further study the scope and versatility of building block 5, we decided to
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