Category: 85618-21-9

Breyton, Cecile published the artcileMicellar and biochemical properties of (hemi)fluorinated surfactants are controlled by the size of the polar head, Category: alcohols-buliding-blocks, the publication is Biophysical Journal (2009), 97(4), 1077-1086, database is CAplus and MEDLINE.

Surfactants with fluorinated and hemifluorinated alkyl chains have yielded encouraging results in terms of membrane protein stability; however, the mols. used hitherto have either been chem. heterogeneous or formed heterogeneous micelles. A new series of surfactants whose polar head size is modulated by the presence of one, two, or three glucose moieties has been synthesized. Anal. ultracentrifugation and small-angle neutron scattering show that fluorinated surfactants whose polar head bears a single glucosyl group form very large cylindrical micelles, whereas those with two or three glucose moieties form small, homogeneous, globular micelles. We studied the homogeneity and stability of the complexes formed between membrane proteins and these surfactants by using bacteriorhodopsin and cytochrome b₆f as models. Homogeneous complexes were obtained only with surfactants that form homogeneous micelles. Surfactants bearing one or two glucose moieties were found to be stabilizing, whereas those with three moieties were destabilizing. Fluorinated and hemifluorinated surfactants with a two-glucose polar head thus appear to be very promising mols. for biochem. applications and structural studies. They were successfully used for cell-free synthesis of the ion channel MscL.

Biophysical Journal published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jin, Yongdong published the artcileBacteriorhodopsin-monolayer-based planar metal-insulator-metal junctions via biomimetic vesicle fusion: preparation, characterization, and bio-optoelectronic characteristics, Related Products of alcohols-buliding-blocks, the publication is Advanced Functional Materials (2007), 17(8), 1417-1428, database is CAplus.

A reliable and reproducible method for preparing bacteriorhodopsin (bR)-containing metal-biomol.-monolayer-metal planar junctions via vesicle fusion tactics and soft deposition of Au top electrodes is reported. Optimum monolayer and junction preparations, including contact effects, are discussed. The electron-transport characteristics of bR-containing membranes are studied systematically by incorporating native bR or artificial bR pigments derived from synthetic retinal analogs, into single solid-supported lipid bilayers. Current-voltage (I-V) measurements at ambient conditions show that a single layer of such bR-containing artificial lipid bilayers pass current in solid electrode/bilayer/solid electrode structures. The current is passed only if retinal or its analog is present in the protein. Furthermore, the preparations show photoconductivity as long as the retinal can isomerize following light absorption. Optical characterization suggests that the junction photocurrents might be associated with a photochem. induced M-like intermediate of bR. I-V measurements along with theor. estimates reveal that electron transfer through the protein is over four orders of magnitude more efficient than what would be estimated for direct tunneling through 5 nm of water-free peptides. The authors’ results furthermore suggest that the light-driven proton-pumping activity of the sandwiched solid-state bR monolayer contributes negligibly to the steady-state light currents that are observed, and that the orientation of bR does not significantly affect the observed I-V characteristics.

Advanced Functional Materials published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ryan, Timothy M. published the artcileSmall Amphipathic Molecules Modulate Secondary Structure and Amyloid Fibril-forming Kinetics of Alzheimer Disease Peptide Aβ_1-42, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Journal of Biological Chemistry (2012), 287(20), 16947-16954, database is CAplus and MEDLINE.

Amyloid fibril formation is associated with a number of debilitating systemic and neurodegenerative diseases. One of the most prominent is Alzheimer disease in which aggregation and deposition of the Aβ peptide occur. Aβ is widely considered to mediate the extensive neuronal loss observed in this disease through the formation of soluble oligomeric species, with the final fibrillar end product of the aggregation process being relatively inert. Factors that influence the aggregation of these amyloid-forming proteins are therefore very important. The authors have screened a library of 96 amphipathic mols. for effects on Aβ_1-42 aggregation and self-association The authors find, using thioflavin T fluorescence and electron microscopy assays, that 30 of the mols. inhibit the aggregation process, whereas 36 activate fibril formation. Several activators and inhibitors were subjected to further anal. using anal. ultracentrifugation and CD. Activators typically display a 1:10 peptide:detergent stoichiometry for maximal activation, whereas the inhibitors are effective at a 1:1 stoichiometry. Anal. ultracentrifugation and CD experiments show that activators promote a mixture of unfolded and β-sheet structures and rapidly form large aggregates, whereas inhibitors induce α-helical structures that form stable dimeric/trimeric oligomers. The results suggest that Aβ_1-42 contains at least one small mol. binding site, which modulates the secondary structure and aggregation processes. Further studies of the binding of these compounds to Aβ may provide insight for developing therapeutic strategies aimed at stabilizing Aβ in a favorable conformation.

Journal of Biological Chemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tamargo Santos, Beatriz published the artcileRemote induction of cellular immune response in mice by anti-meningococcal nanocochleates – nanoproteoliposomes, Product Details of C14H28O5S, the publication is Science of the Total Environment (2019), 1055-1063, database is CAplus and MEDLINE.

New adjuvant formulations, based on proteoliposomes <40 nm and cochleates <100 nm, without Al(OH)₃ adjuvant, were evaluated regarding their ability to generate Th1 immune response through a Delayed-Type Hypersensitivity Test, at the mouse model, by using a Neisseria meningitidis B protein complex as antigen. The formulations were administered by i.m. (IM) (2 inoculations – at baseline and after 14 days) and intranasal (IN) (3 inoculations at 7 days) immunization pathways. All IM immunized groups were able to induce similar response to these formulations as well as to VA-MENGOC-BC vaccine – containing Al(OH)₃ adjuvant (used as pos. control of the trial). In all groups, the induced inflammation (IP) rate was statistically higher than in the neg. control group (CN) (p < 0.05). Immunogenicity, measured by HSR and CD4⁺ lymphocyte increase was equivalent to the control vaccine and most important, granuloma reactogenicity at the site of injection was eliminated, fact demonstrated by histol. study. All groups of animals immunized by IN route showed HSR reactions and statistically significant differences with respect to the CN group. However, IP values were lower, with statistical differences (p < 0.05) for the same adjuvant formulation IM administered, except the AIF2-nCh formulation that generated statistically similar induction (p > 0.05) by both immunization pathways, suggesting it to be the best candidate for the next IN trial. Proteoliposome and cochleate formulations tested were able to mount potent Th1 immune response, equivalent to the original vaccine formulation, with the advantage of less reactogenicity in the site of the injection, caused by the toxicity of Al(OH)₃ adjuvant gel.

Science of the Total Environment published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C4H11NO, Product Details of C14H28O5S.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Troutman, Jerry M. published the artcileTuning the Production of Variable Length, Fluorescent Polyisoprenoids Using Surfactant-Controlled Enzymatic Synthesis, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biochemistry (2015), 54(18), 2817-2827, database is CAplus and MEDLINE.

Bactoprenyl diphosphate (BPP), a two-E eight-Z configuration C₅₅ isoprenoid, serves as a critical anchor for the biosynthesis of complex glycans central to bacterial survival and pathogenesis. BPP is formed by the polymerase undecaprenyl pyrophosphate synthase (UppS), which catalyzes the elongation of a single farnesyl diphosphate (FPP) with eight Z-configuration isoprene units from eight isopentenyl diphosphates. In vitro anal. of UppS and other polyprenyl diphosphate synthases requires the addition of a surfactant such as Triton X-100 to stimulate the release of the hydrophobic product from the enzyme for effective and efficient turnover. Here using a fluorescent 2-nitrileanilinogeranyl diphosphate analog of FPP, we have found that a wide range of surfactants can stimulate release of product from UppS and that the structure of the surfactant has a major impact on the lengths of products produced by the protein. Of particular importance, shorter chain surfactants promote the release of isoprenoids with four to six Z-configuration isoprene additions, while larger chain surfactants promote the formation of natural isoprenoid lengths (8Z) and larger. We have found that the product chain lengths can be readily controlled and coarsely tuned by adjusting surfactant identity, concentration, and reaction time. We have also found that binary mixtures of just two surfactants can be used to fine-tune isoprenoid lengths. The surfactant effects discovered do not appear to be significantly altered with an alternative isoprenoid substrate. However, the surfactant effects do appear to be dependent on differences in UppS between bacterial species. This work provides new insights into surfactant effects in enzymol. and highlights how these effects can be leveraged for the chemoenzymic synthesis of otherwise difficult to obtain glycan biosynthesis probes. This work also provides key reagents for the systematic anal. of structure-activity relationships between glycan biosynthesis enzymes and isoprenoid structure.

Biochemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C15H20O6, Application of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kaufmann, Thomas C. published the artcileA novel method for detergent concentration determination, Recommanded Product: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biophysical Journal (2006), 90(1), 310-317, database is CAplus and MEDLINE.

A fast and precise method for detergent concentration determination is presented. A small droplet of the detergent solution is deposited on a piece of Parafilm M and side views are recorded by two orthogonally arranged TV cameras. The droplet contours are then approximated by ellipses to determine the contact angles. Comparison of the observed contact angle values to calibrated standard curves of known detergent concentrations gives the concentration of the detergent assessed. A range of commonly used detergents was studied to demonstrate the reproducibility and precision of this simple method. As a first application, the detergent binding capacity of the Escherichia coli galactose/proton symporter (GalP) was assessed. Aggregation of GalP was observed when <260±5 dodecyl-β-D-maltoside mols. were bound to one GalP mol. These measurements document the efficacy of the drop-shape based detergent concentration determination described.

Biophysical Journal published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Recommanded Product: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Takeda, Kazuo published the artcileFe(II)/Cu(I)-dependent P-type ATPase activity in the liver of Long-Evans cinnamon rats, Quality Control of 85618-21-9, the publication is Life Sciences (2005), 76(19), 2203-2209, database is CAplus and MEDLINE.

This study examined Fe(II)-dependent ATPase activity in OTG (octylthioglucoside)-treated microsomes isolated from Wistar and LEC rats. The ATPase activity of the liver OTG-microsomes from Wistar rats increased sharply in the 5-150 μM range of Fe(II) with a K_0.5 value of 23.9 ± 3.6 μM, while the activity of LEC rat liver microsomes increased with increasing Fe(II) up to 500 μM with a K_0.5 value of 64.4 ± 8.1 μM. The K_0.5 values for Fe(II)-dependent ATPase activity of spleen OTG-microsomes were nearly identical at 59.3 μM in the Wistar rat and 63.7 μM in the LEC rats with a similar level of activity at each Fe(II) concentration in both strains of animals. These results indicated that there are two types of Fe(II)-dependent ATPase with different Fe(II) sensitivity, a high sensitive (H) and a low sensitive (L) type, and that the H-type activity was specific to the liver. The H-type activity was, however, deficient in the liver of LEC rats that accumulate copper and iron in hepatocytes as a result of mutations in the Wilson’s disease protein (WNDP). On the basis of these results, together with the similarity in optimal conditions required for full activity of the enzyme, we conclude that the Fe(II)-dependent ATPase (H-type) and WNDP may be identical.

Life Sciences published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H10O4S2, Quality Control of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tribet, C. published the artcileThermodynamic Characterization of the Exchange of Detergents and Amphipols at the Surfaces of Integral Membrane Proteins, Quality Control of 85618-21-9, the publication is Langmuir (2009), 25(21), 12623-12634, database is CAplus and MEDLINE.

The aggregation of integral membrane proteins (IMPs) in aqueous media is a significant concern for mechanistic investigations and pharmaceutical applications of this important class of proteins. Complexation of IMPs with amphiphiles, either detergents or short amphiphilic polymers known as amphipols (APols), renders IMPs water-soluble It is common knowledge that IMP-detergent complexes are labile, while IMP-APol complexes are exceptionally stable and do not dissociate even under conditions of extreme dilution To understand the thermodn. origin of this difference in stability and to guide the design of new APols, the authors have studied by isothermal titration calorimetry (ITC) the heat exchanges during two reciprocal processes, the “trapping” of detergent-solubilized IMPs in APols and the “stripping” of IMP-APol complexes by detergents, using two IMPs (the transmembrane domain of porin OmpA from Escherichia coli and bacteriorhodopsin from Halobacterium salinarium), two APols [an anionic polymer derived from acrylic acid (A8-35) and a cationic phosphorylcholine-based polymer (C22-43)], and two neutral detergents [n-octyl thioglucoside (OTG) and n-octyltetraethylene glycol (C₈E₄)]. In the presence of detergent, free APols and IMP-APol complexes form mixed particles, APol-detergent and IMP-APol-detergent, resp., according to the regular mixing model. Diluting IMP-APol-detergent complexes below the critical micellar concentration (CMC) of the detergent triggers the dispersion of detergent mols. as monomers, a process characterized by an enthalpy of demicellization. The enthalpy of APol ↔ detergent exchange on the hydrophobic surface of IMPs is negligibly small, an indication of the similarity of the mol. interactions of IMPs with the two types of amphiphiles. The enhanced stability against dilution of IMP-APol complexes, compared to IMP-detergent ones, originates from the difference in entropy gain achieved upon release in water of a few APol mols. (in the case of IMP-APol complexes) or several hundred detergent mols. (in the case of IMP-detergent complexes). The data account both for the stability of IMP-APols complexes in the absence of detergent and for the ease with which detergents displace APols from the surface of proteins.

Langmuir published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C18H34N4O5S, Quality Control of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Spell, Mark L. published the artcileA Visible-Light-Promoted O-Glycosylation with a Thioglycoside Donor, Quality Control of 85618-21-9, the publication is Angewandte Chemie, International Edition (2016), 55(22), 6515-6519, database is CAplus and MEDLINE.

Visible-light irradiation of 4-p-methoxyphenyl-3-butenylthioglucoside donors in the presence of Umemoto’s reagent and alc. acceptors serves as a mild approach to O-glycosylation. Visible-light photocatalysts are not required for activation, and alkyl- and arylthioglycosides not bearing the p-methoxystyrene are inert to these conditions. Exptl. and computational evidence for an intervening electron donor-acceptor complex, which is necessary for reactivity, is provided. Yields with primary, secondary, and tertiary alc. acceptors range from moderate to high. Complete β-selectivity can be attained through neighboring-group participation.

Angewandte Chemie, International Edition published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C8H7N3, Quality Control of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gohon, Yann published the artcileBacteriorhodopsin/amphipol complexes: structural and functional properties, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biophysical Journal (2008), 94(9), 3523-3537, database is CAplus and MEDLINE.

The membrane protein bacteriorhodopsin (BR) can be kept soluble in its native state for months in the absence of detergent by amphipol (APol) A8-35, an amphiphilic polymer. After an actinic flash, A8-35-complexed BR undergoes a complete photocycle, with kinetics intermediate between that in detergent solution and that in its native membrane. BR/APol complexes form well defined, globular particles comprising a monomer of BR, a complete set of purple membrane lipids, and, in a peripheral distribution, ∼2 g APol/g BR, arranged in a compact layer. In the absence of free APol, BR/APol particles can autoassoc. into small or large ordered fibrils.

Biophysical Journal published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts