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Search for "lipids" in Full Text gives 90 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

  • Jens Frackenpohl,
  • David M. Barber,
  • Guido Bojack,
  • Birgit Bollenbach-Wahl,
  • Ralf Braun,
  • Rahel Getachew,
  • Sabine Hohmann,
  • Kwang-Yoon Ko,
  • Karoline Kurowski,
  • Bernd Laber,
  • Rebecca L. Mattison,
  • Thomas Müller,
  • Anna M. Reingruber,
  • Dirk Schmutzler and
  • Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

Graphical Abstract
  • 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
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Published 01 Mar 2024

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Graphical Abstract
  • 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
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Published 01 Mar 2024

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

  • Ghenwa Nasr,
  • Hélène Greige-Gerges,
  • Sophie Fourmentin,
  • Abdelhamid Elaissari and
  • Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

Graphical Abstract
  • %, 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
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Published 17 Oct 2023

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

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  • 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
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Published 08 Sep 2023

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

  • Valeriy O. Filimonov,
  • Alexandra I. Topchiy,
  • Vladimir G. Ilkin,
  • Tetyana V. Beryozkina and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

Graphical Abstract
  • 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
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Published 08 Aug 2023

Cyclodextrins as building blocks for new materials

  • Miriana Kfoury and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

Graphical Abstract
  • 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
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Published 19 Jun 2023

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

  • Nicoleta G. Hădărugă,
  • Gabriela Popescu,
  • Dina Gligor (Pane),
  • Cristina L. Mitroi,
  • Sorin M. Stanciu and
  • Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

Graphical Abstract
  • 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
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Published 28 Mar 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

Graphical Abstract
  • (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
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Published 02 Feb 2023

Digyalipopeptide A, an antiparasitic cyclic peptide from the Ghanaian Bacillus sp. strain DE2B

  • Adwoa P. Nartey,
  • Aboagye K. Dofuor,
  • Kofi B. A. Owusu,
  • Anil S. Camas,
  • Hai Deng,
  • Marcel Jaspars and
  • Kwaku Kyeremeh

Beilstein J. Org. Chem. 2022, 18, 1763–1771, doi:10.3762/bjoc.18.185

Graphical Abstract
  • 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
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Published 28 Dec 2022

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

Graphical Abstract
  • % 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
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Published 22 Jun 2022

Menadione: a platform and a target to valuable compounds synthesis

  • Acácio S. de Souza,
  • Ruan Carlos B. Ribeiro,
  • Dora C. S. Costa,
  • Fernanda P. Pauli,
  • David R. Pinho,
  • Matheus G. de Moraes,
  • Fernando de C. da Silva,
  • Luana da S. M. Forezi and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Graphical Abstract
  • (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
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Published 11 Apr 2022

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

  • Ruan Carlos B. Ribeiro,
  • Patricia G. Ferreira,
  • Amanda de A. Borges,
  • Luana da S. M. Forezi,
  • Fernando de Carvalho da Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

Graphical Abstract
  • 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
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Published 05 Jan 2022

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

  • Nikita Brodyagin,
  • Martins Katkevics,
  • Venubabu Kotikam,
  • Christopher A. Ryan and
  • Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

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Published 19 Jul 2021

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

  • Roslyn M. Ray,
  • Anders Højgaard Hansen,
  • Maria Taskova,
  • Bernhard Jandl,
  • Jonas Hansen,
  • Citra Soemardy,
  • Kevin V. Morris and
  • Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

Graphical Abstract
  • 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
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Published 26 Apr 2021

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

  • Masayori Hagimori,
  • Estefanía E. Mendoza-Ortega and
  • Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

Graphical Abstract
  • 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
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Published 19 Feb 2021

Selected peptide-based fluorescent probes for biological applications

  • Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

Graphical Abstract
  • 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
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Published 03 Dec 2020

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

  • Thomas Holmstrøm,
  • Daniel Raydan and
  • Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

Graphical Abstract
  • 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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Published 17 Nov 2020

A consensus-based and readable extension of Linear Code for Reaction Rules (LiCoRR)

  • Benjamin P. Kellman,
  • Yujie Zhang,
  • Emma Logomasini,
  • Eric Meinhardt,
  • Karla P. Godinez-Macias,
  • Austin W. T. Chiang,
  • James T. Sorrentino,
  • Chenguang Liang,
  • Bokan Bao,
  • Yusen Zhou,
  • Sachiko Akase,
  • Isami Sogabe,
  • Thukaa Kouka,
  • Elizabeth A. Winzeler,
  • Iain B. H. Wilson,
  • Matthew P. Campbell,
  • Sriram Neelamegham,
  • Frederick J. Krambeck,
  • Kiyoko F. Aoki-Kinoshita and
  • Nathan E. Lewis

Beilstein J. Org. Chem. 2020, 16, 2645–2662, doi:10.3762/bjoc.16.215

Graphical Abstract
  • recommended preserving this symbol use since it is human and computer-readable and does not overlap with any notation in the original Linear Code. Recommendation 3 – “Number.” “ # ” was defined to combine glycans with glycosides other than amino acids and lipids (Table 3: GR1). Krambeck et al. use it to
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Published 27 Oct 2020

Computational tools for drawing, building and displaying carbohydrates: a visual guide

  • Kanhaya Lal,
  • Rafael Bermeo and
  • Serge Perez

Beilstein J. Org. Chem. 2020, 16, 2448–2468, doi:10.3762/bjoc.16.199

Graphical Abstract
  • together either linearly or branched); (ii) polysaccharides (for glycan chains composed of more than ten monosaccharides); (iii) glycoconjugates (where the glycan chains are covalently linked to proteins (glycoproteins), lipids (glycolipids). The complexity of glycans is a consequence of their branched
  • assembles data resources ranging from glycoscience standard ontologies to pathologies associated with glycans. GlyCosmos is recognized as the official portal of the Japanese Society for Carbohydrate Research and provides information about genes, proteins, lipids, pathways and diseases. GlyTouCan (Figure 5
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Published 02 Oct 2020

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

  • Patrizia Andreozzi,
  • Lorenza Tamberi,
  • Elisamaria Tasca,
  • Gina Elena Giacomazzo,
  • Marta Martinez,
  • Mirko Severi,
  • Marco Marradi,
  • Stefano Cicchi,
  • Sergio Moya,
  • Giacomo Biagiotti and
  • Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

Graphical Abstract
  • range of biomolecules: amino acids [8], peptides [9], glycosides [10], nucleosides/nucleotides [11], and lipids [12]. Also, protein-based nano-bio-conjugates [13] have been prepared by ball milling, retaining the native properties of the proteins after mechanochemical synthesis. Boronic acids and their
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Published 11 Sep 2020

Tools for generating and analyzing glycan microarray data

  • Akul Y. Mehta,
  • Jamie Heimburg-Molinaro and
  • Richard D. Cummings

Beilstein J. Org. Chem. 2020, 16, 2260–2271, doi:10.3762/bjoc.16.187

Graphical Abstract
  • structural informatics tools. Keywords: data analysis; glycan binding; glycan microarray; glycomics; informatics; Introduction Glycans represent a major type of biomolecule in all living things, along with DNA, RNA, lipids and proteins [1]. In mammals, glycans commonly occur as post-translational
  • modifications of proteins (glycoproteins), but they are also linked to lipids (glycolipids) and occur as free molecules. Such glycomolecules have vital roles in a wide range of physiological functions and also participate in many pathologic conditions [2]. Some classic examples of important glycans include the
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Published 10 Sep 2020

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

  • Esra Demir,
  • Ozlem Sari,
  • Yasin Çetinkaya,
  • Ufuk Atmaca,
  • Safiye Sağ Erdem and
  • Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

Graphical Abstract
  • natural products ranging from small molecules, such as sugars, lipids and amino acids to huge molecules [56]. Computational results A detailed mechanistic investigation of the synthesis of oxazolidinone and five-membered cyclic carbonate derivatives by the reaction between epoxide 7f and CSI has been
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Published 21 Jul 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

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Published 26 Jun 2020

Steroid diversification by multicomponent reactions

  • Leslie Reguera,
  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

Graphical Abstract
  • two different steroidal scaffolds [65], but it failed for the ligation of larger peptides to steroids due to the poor solubility of the former ones. In this sense, Rivera’s group introduced a solid-phase multicomponent procedure enabling the conjugation of steroids and lipids to peptides longer than
  • conjugation at the N-terminus required microwave irradiation due to the bulkier character of the amino component. Besides steroids, the method worked well with varied boronic acids, including those bearing fluorescent labels, lipids and PEG chains, thus providing a new class of biomolecular conjugates showing
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Published 06 Jun 2019

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

  • Dimitri Fayolle,
  • Nathalie Berthet,
  • Bastien Doumeche,
  • Olivier Renaudet,
  • Peter Strazewski and
  • Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

Graphical Abstract
  • Lipids (Alabaster, AL, USA). 2,3,4,6-Tetra-O-acetyl-α--glucopyranosyl bromide and N-acetyl--glucosamine were from Carbosynth (San Diego, CA, USA). Wheat germ agglutinin (WGA), horseradish peroxidase-labelled WGA (WGA-HRP), bovine serum albumin (BSA) and SIGMA FAST O-phenylenediamine dihydrochloride (OPD
  • : Giant vesicles (GVs) were prepared by the natural swelling method [23]. Lipids (mixture of commercial POPC and n-alkyl thioglycosides 5 or 8) were dissolved in methanol (typically, 2 mL) in a 10 mL round-bottom flask. The solvent was completely evaporated under reduced pressure using a rotatory
  • . a–e) POPC/8, 9:1 molar ratio; f and g) pure 8; h) 5/8, 1:1 molar ratio; i) pure 5; All the samples were prepared with 1 mM lipids and stained with NileRed® (1 mM in EtOH, 1 µL, λ[excit] = 561 nm) before the microscopic observation. Red arrows are used to indicate small GVs. The scale bar is 20 µm
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Published 17 Apr 2019
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