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

• 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

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

• % 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

• 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

• (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

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

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• first start to grow and divide in an unregulated and error-prone way, relying extensively on environmental conditions and external stimuli. (b) After a major prebiotic transition (blue arrow ‘MT’), the first self-producing protocells appeared, able to endogenously synthesise membrane lipids and other

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

• to understand the way proteins interact with membrane lipids, and our knowledge in the domain is still far from complete. There exist many models describing the operation (including ideas about the asymmetry of the bilayer, its local changes and lipid rafts). Work exploring the way proteins are

Aggregation behaviour of a single-chain, phenylene-modified bolalipid and its miscibility with classical phospholipids

• Simon Drescher,
• Vasil M. Garamus,
• Christopher J. Garvey,
• Annette Meister and
• Alfred Blume

Beilstein J. Org. Chem. 2017, 13, 995–1007, doi:10.3762/bjoc.13.99

• -C18pPhC18-PC is partially miscible with saturated phosphatidylcholines; however, closed lipid vesicles with an increased thermal stability were not found. Instead, bilayer fragments and disk-like aggregates are formed. Keywords: aggregation behaviour; bolaamphiphiles; bolalipids; membrane lipids; mixing

• in the chemical structure of those archaeal membrane lipids: the alkyl chains are connected via ether linkages in the inverse sn-2,3 configuration to the glycerol, the alkyl chains sometimes contain a varying number of cyclopentane rings or several methyl branches [2][3], and some of the archaeal

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• constituents, resulting in highly characteristic effects on the packing and lateral organization of the membrane lipids and proteins [1][10][11][12][13]. Even very small alterations in the molecular structure of cholesterol cause large differences in the interaction with phospholipids and its membrane’s

• barrier function. Interestingly, not only modifications in the tetracyclic sterol ring system lead to pronounced changes of the molecular membrane architecture and of the interactions between the respective sterol and membrane lipids and proteins [14][15][16][17], but also the iso-branched side chain of

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

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

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• NPC-like HepG2 cells via asialoglycoprotein receptor (ASGPR)-mediated endocytosis. Keywords: asialoglycoprotein receptor; cholesterol; cyclodextrin; lactose; Niemann–Pick type C disease; Introduction The Niemann–Pick type C (NPC) disease is a lipid storage disorder with the accumulation of membrane

• lipids such as cholesterol and multiple sphingolipids especially in lysosomes. The excessive accumulation of these lipids results in a progressive neurologic and visceral dysfunction [1][2][3]. A mutation in the NPC1 and/or NPC2 gene causes the NPC disease. The majority of the mutations occur in the NPC1

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• with lipids (49%) and carbohydrates (8%) and as the fraction of cholesterol is 25% of total membrane lipids [54], the proposed explanation is based on the specific interaction of natural CDs with the erythrocyte membrane components. Indeed, α- and β-CD are excellently suited to solubilize phospholipids

• affinity with sphingolipids than with other membrane phospholipids. As extension of this work, Huang and London highlighted the possibility of preparing asymmetric vesicles during the exchange of membrane lipids between different vesicles by selective inclusion of phospholipids and/or cholesterol into the

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

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