Tag: M.W=300-350

Kinzel, Olaf published the artcileSynthesis of a functionalized high affinity mannose receptor ligand and its application in the construction of peptide-, polyamide- and PNA-conjugates, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Journal of Peptide Science (2003), 9(6), 375-385, database is CAplus and MEDLINE.

The synthesis of a high affinity mannose receptor ligand, appropriately functionalized for chemoselective ligation with an antigen or DNA-binding moieties is described. By a combination of solid- and solution-phase chem. a versatile synthesis of the target structure was accomplished. Examples of subsequent ligation reactions are described.

Journal of Peptide Science published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Safety of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

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

Kaur, Gurpreet published the artcileSubstituent effect on anthracene-based bisboronic acid glucose sensors, Application In Synthesis of 673456-16-1, the publication is Tetrahedron (2006), 62(11), 2583-2589, database is CAplus.

Earlier the authors communicated an anthracene-based bisboronic acid sensor for glucose. Aimed at understanding the substituent effect, the authors have introduced various functional groups, such as the cyano, nitro, and fluoro group on the boronic acid moiety of this glucose sensor. Fluorescent binding studies indicated that the cyano-substituted sensor has the highest affinity (K 2540 M^-1) for glucose, but the lowest selectivity (three-fold over fructose); the fluoro-substituted compound shows the lowest affinity (630 M^-1) and a modest selectivity (15-fold over fructose); and the unsubstituted one shows the highest selectivity over fructose (43-fold) and a modest affinity (1472 M^-1).

Tetrahedron published new progress about 673456-16-1. 673456-16-1 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Bromide,Boronic acid and ester,Benzyl bromide,Benzene,Boronic Acids,Boronic acid and ester,, name is 2-(2-(Bromomethyl)-4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane, and the molecular formula is C12H15BBrFO2, Application In Synthesis of 673456-16-1.

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

Lape, Michael published the artcileMolecular determinants of sarco/endoplasmic reticulum calcium ATPase inhibition by hydroquinone-based compounds, Computed Properties of 903-19-5, the publication is Proteins: Structure, Function, and Bioinformatics (2008), 70(3), 639-649, database is CAplus and MEDLINE.

The ion transport activity of the sarco/endoplasmic reticulum calcium ATPase (SERCA) is specifically and potently inhibited by the small mol. 2,5-di-tert-butylhydroquinone (BHQ). In this study, we investigated the relative importance of the nature and position of BHQ’s four substituents for enzyme inhibition by employing a combination of exptl. and computational techniques. The inhibitory potencies of 21 com. available or synthesized BHQ derivatives were determined in ATPase activity assays, and 11 compounds were found to be active. Maximum inhibitory potency was observed in compounds with two para hydroxyl groups, whereas BHQ analogs with only one hydroxyl group were still active, albeit with a reduced potency. The results also demonstrated that two alkyl groups were an absolute requirement for activity, with the most potent compounds having 2,5-substituents with four or five carbon atoms at each position. Using the program GOLD in conjunction with the ChemScore scoring function, the structures of the BHQ analogs were docked into the crystal structure of SERCA mimicking the enzyme’s E₂ conformation. Anal. of the docking results indicated that inhibitor binding to SERCA was primarily mediated by a hydrogen bond between a hydroxyl group and Asp59 and by hydrophobic interactions involving the bulky inhibitor alkyl groups. Attempts to dock BHQ into crystal structures corresponding to the E₁ conformation of the enzyme failed, because the conformational changes accompanying the E₂/E₁ transition severely restricted the size of the binding site, suggesting that BHQ stabilizes the enzyme in its E₂ form. The potential role of Glu309 in enzyme inhibition is discussed in the context of the computational results. The docking scores correlated reasonably well with the measured inhibitory potencies and allowed the distinction between active and inactive compounds, which is a key requirement for future virtual screening of large compound databases for novel SERCA inhibitors.

Proteins: Structure, Function, and Bioinformatics published new progress about 903-19-5. 903-19-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 2,5-Bis(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol, and the molecular formula is C22H38O2, Computed Properties of 903-19-5.

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

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

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

Lo Leggio, Leila published the artcileThe Structure and Specificity of Escherichia coli Maltose Acetyltransferase Give New Insight into the LacA Family of Acyltransferases, Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Biochemistry (2003), 42(18), 5225-5235, database is CAplus and MEDLINE.

The crystallog. three-dimensional structure of the Escherichia coli maa gene product, previously identified as a maltose O-acetyltransferase (MAT) [Brand, B., and Boos, W. (1991) J. Biol. Chem. 266, 14113-14118] has been determined to 2.15 Å resolution by the single anomalous dispersion method using data from a crystal cocrystd. with trimethyllead acetate. It is shown here that MAT acetylates glucose exclusively at the C6 position and maltose at the C6 position of the nonreducing end glucosyl moiety. Furthermore, MAT shows higher affinity toward artificial substrates containing an alkyl or hydrophobic chain as well as a glucosyl unit. The presence of a long hydrophobic patch near the acceptor site provides the structural explanation for this preference. The three-dimensional structure reveals the expected trimeric left-handed parallel β-helix structure found in all other known hexapeptide repeat enzymes. In particular, the structure shows similarities both overall and at the putative active site to the recently determined structure of galactoside acetyltransferase (GAT), the lacA gene product [Wang, X.-G., Olsen, L. R., and Roderick, S. L. (2002) Structure 10, 581-588]. The structure, together with the new biochem. data, suggests that GAT and MAT are more closely related than previously thought and might have similar cellular functions. However, while GAT is specific for acetylation of galactosyl units, MAT is specific for glucosyl units and is able to acetylate maltooligosaccharides, an important property for biotechnol. applications. Structural differences at the acceptor site reflect the differences in substrate specificity.

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 C14H28O5S, Name: (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