Tag: 300-400

Synthesis and conformational preferences of short analogs of antifreeze glycopeptides (AFGP) was written by Urbanczyk, Malgorzata;Jewginski, Michal;Krzciuk-Gula, Joanna;Gora, Jerzy;Latajka, Rafal;Sewald, Norbert. And the article was included in Beilstein Journal of Organic Chemistry in 2019.Recommanded Product: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate This article mentions the following:

Antifreeze glycoproteins are a class of biol. agents which enable living at temperatures below the f.p. of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr*-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the mol. as well an on the stereochem. of amino acid residues. The desired monoglycosylated analogs with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational NMR (NMR) studies of the designed analogs have shown a strong influence of the stereochem. of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Recommanded Product: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Recommanded Product: (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Influence of the Internal Structure and Intermolecular Interactions on the Correlation between Structural (α) and Secondary (β-JG) Relaxation below the Glass Transition Temperature in Neat Probucol and Its Binary Mixtures with Modified Saccharides was written by Minecka, A.;Tarnacka, M.;Jurkiewicz, K.;Hachula, B.;Kaminski, K.;Paluch, M.;Kaminska, E.. And the article was included in Journal of Physical Chemistry B in 2020.Related Products of 4163-60-4 This article mentions the following:

Broadband dielec. spectroscopy (BDS) has been used to study the mol. dynamics and aging process in neat probucol (PRO) as well as its binary mixtures with selected acetylated saccharides. In particular, we applied the Casalini and Roland approach to determine structural relaxation times in the glassy state of the examined systems (so-called isostructural times, τ_iso). Next, using the calculated τ_iso, primitive relaxation times of the coupling model were obtained and compared to the exptl. secondary β (Johari-Goldstein (JG) type) relaxation times. Interestingly, it turned out that there is a correlation between the β-JG and the structural (α)-relaxation processes below the glass transition temperature (T < T_g) in each investigated sample. This is a new observation compared to previous studies demonstrating that such a relationship exists only in the supercooled liquid state of neat PRO. Moreover, it was revealed that the stretching parameters obtained from the aging procedure are very close to the ones determined by fitting the dielec. data above the T_g with the use of the Kohlrausch-Williams-Watts function, indicating that the aging process is governed by the α-relaxation. Complementary Fourier transform IR and X-ray diffraction measurements allowed us to find a possible reason for these findings. It was demonstrated that although there are very weak intermol. interactions between PRO and modified saccharides, the intra- and intermol. structure of PRO is practically unaffected by the presence of modified saccharides. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Related Products of 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Related Products of 4163-60-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Intrapopulation and temporal differences of phthalate concentrations in North Atlantic fin whales (Balaenoptera physalus) was written by Garcia-Garin, Odei;Sahyoun, Wissam;Net, Sopheak;Vighi, Morgana;Aguilar, Alex;Ouddane, Baghdad;Vikingsson, Gisli A.;Chosson, Valerie;Borrell, Asuncion. And the article was included in Chemosphere in 2022.Reference of 84-61-7 This article mentions the following:

The fin whale (Balaenoptera physalus) is a migratory filter-feeding species that is susceptible to ingest plastics while lunge feeding across the oceans. Plastic additives, such as phthalates, are compounds that are added to plastics to give them specific characteristics, such as flexibility. These so-called plasticizers are currently raising major concern because of their potential adverse effects on marine fauna. However, little is known about phthalate concentrations in tissues of baleen whales as well as their potential relation with biol. variables (i.e., sex, body length and age) and their trends with time. In this study, we assessed the concentration of 13 phthalates in the muscle of 31 fin whales sampled in the feeding grounds off western Iceland between 1986 and 2015. We detected 5 of the 13 phthalates investigated, with di-n-butylphthalate (DBP), diethylphthalate (DEP) and bis(2-ethylhexyl) phthalate (DEHP) being the most abundant. None of the biol. variables examined showed a statistically significant relationship with phthalate concentrations Also, phthalate concentrations did not significantly vary over the 29-yr period studied, a surprising result given the global scenario of increasing plastic pollution in the seas. The lack of time trends in phthalate concentration may be due in part to the fact that phthalates also originate from other sources. Although no adverse effects of phthalates on fin whales have been detected to date, further monitoring of these pollutants is required to identify potential toxic effects in the future. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7Reference of 84-61-7).

Dicyclohexyl phthalate (cas: 84-61-7) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Reference of 84-61-7

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Discovery of the Chemical Function of Glycosidases: Design, Synthesis, and Evaluation of Mass-Differentiated Carbohydrate Libraries was written by Yu, Yang;Ko, Kwang-Seuk;Zea, Corbin J.;Pohl, Nicola L.. And the article was included in Organic Letters in 2004.Category: esters-buliding-blocks This article mentions the following:

Discovery of the catalytic chem. function of the many putative glycosidases coded in genomes currently relies on individual testing of possible substrates, usually as their p-nitrophenol conjugate. Herein, the authors present an alternative chem. proteomics approach using a synthetic mass-differentiated heat-stable substrate library with mass spectrometry readout. Library components do not serve as reaction inhibitors and both primary and secondary enzyme substrates can be delineated. In the experiment, the researchers used many compounds, for example, (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5Category: esters-buliding-blocks).

(2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Category: esters-buliding-blocks

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Both chemical and non-chemical steps limit the catalytic efficiency of family 4 glycoside hydrolases was written by Sannikova, Natalia;Gerak, Chloe A. N.;Shidmoossavee, Fahimeh S.;King, Dustin T.;Shamsi Kazem Abadi, Saeideh;Lewis, Andrew R.;Bennet, Andrew J.. And the article was included in Biochemistry in 2018.Computed Properties of C16H22O11 This article mentions the following:

The glycoside hydrolase family 4 (GH4) α-galactosidase from Citrobacter freundii (MelA) catalyzes the hydrolysis of fluoro-substituted Ph α-D-galactopyranosides by utilizing two cofactors, NAD⁺ and a metal cation, under reducing conditions. In order to refine the mechanistic understanding of this GH4 enzyme, leaving group effects were measured with various metal cations. The derived β_lg value on V/K for strontium activation is indistinguishable from zero (0.05 ± 0.12). Deuterium kinetic isotope effects (KIEs) were measured for the activated substrates 2-fluorophenyl and 4-fluorophenyl α-D-galactopyranosides in the presence of Sr²⁺, Y³⁺, and Mn²⁺, where the isotopic substitution was on the carbohydrate at C-2 and/or C-3. To determine the contributing factors to the virtual transition state (TS) on which the KIEs report, kinetic isotope effects on isotope effects were measured on these KIEs using doubly deuterated substrates. The measured ^DV/K KIEs for MelA-catalyzed hydrolysis of 2-fluorophenyl α-D-galactopyranoside are closer to unity than the measured effects on 4-fluorophenyl α-D-galactopyranoside, irresp. of the site of isotopic substitution and of the metal cation activator. These observations are consistent with hydride transfer at C-3 to the on-board NAD⁺, deprotonation at C-2, and a non-chem. step contributing to the virtual TS for V/K. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Computed Properties of C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Computed Properties of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis was written by Dohi, Hirofumi;Sakurai, Risa;Tamura, Manami;Komai, Ryota;Nishida, Yoshihiro. And the article was included in Journal of Carbohydrate Chemistry in 2021.Formula: C16H22O11 This article mentions the following:

Herein, o-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The o-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglycosides exhibited high reactivity and glycosylation yields when N-iodosuccinimide and trifluoromethanesulfonic acid were used as promoters. Glycosylation with these thioglycosides in dichloromethane showed similar reactivity and stereoselectivity as those of Ph thioglycosides. Glycosylation with per-O-benzyl salicyl-type thioglycosides in dichloromethane showed 1,2-cis-selectivity, while the same reaction in nitriles afforded predominantly 1,2-trans glycosides. In contrast, glycosylation with per-O-benzoyl thioglycosides afforded exclusively 1,2-trans glycosides. These results strongly suggest that salicyl-type thioglycosides can serve as non-malodorous alternatives for Ph thioglycosides. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Formula: C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Formula: C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Efficient and reproducible synthesis of an Fmoc-protected Tn antigen was written by Piazza, Sabrina M.;Reynolds, Michael R.;Chiaramonte, Jonathan;Xu, Peihan;Chapa-Villarreal, Fabiola A.;Trant, John F.. And the article was included in New Journal of Chemistry in 2021.Electric Literature of C16H22O11 This article mentions the following:

This concise total synthesis of the Thomsen-Nouveau (Tn) glycoconjugate was accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-protected serine acceptor. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Electric Literature of C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Electric Literature of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides was written by Liu, Bing;van Mechelen, Jeanine;van den Berg, Richard J. B. H. N.;van den Nieuwendijk, Adrianus M. C. H.;Aerts, Johannes M. F. G.;van der Marel, Gijsbert A.;Codee, Jeroen D. C.;Overkleeft, Herman S.. And the article was included in European Journal of Organic Chemistry in 2019.Synthetic Route of C16H22O11 This article mentions the following:

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bio-organic chem. and medicinal chem., yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation-reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on com. disaccharides, as shown in four examples, as well as on disaccharides that are not com. available and are synthesized for this purpose, as shown by a fifth example. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Synthetic Route of C16H22O11).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Synthetic Route of C16H22O11

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

[Bis(2-methoxyethyl)amino]sulfur trifluoride, the Deoxo-Fluor reagent: application toward one-flask transformations of carboxylic acids to amides was written by White, Jonathan M.;Tunoori, Ashok Rao;Turunen, Brandon J.;Georg, Gunda I.. And the article was included in Journal of Organic Chemistry in 2004.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:

The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. The utility of this reagent was explored for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthesis of disaccharide modified berberine derivatives and their anti-diabetic investigation in zebrafish using a fluorescence-based technology was written by Wang, Lizhen;Kong, Haotian;Jin, Meng;Li, Xiaobin;Stoika, Rostyslav;Lin, Houwen;Liu, Kechun. And the article was included in Organic & Biomolecular Chemistry in 2020.HPLC of Formula: 4163-60-4 This article mentions the following:

Berberine is a naturally occurring isoquinoline alkaloid and has been used as an important functional food additive in China due to its various pharmacol. activities. Berberine exhibits great potential for developing anti-diabetic agents against type 2 diabetes mellitus (T2DM), as it can reduce the blood glucose level in many animal models. However, the low anti-diabetic activity and poor bioavailability of berberine (below 5%) by oral administration significantly limit its practical applications. To solve these problems, this article focuses on the structural modification of berberine using some disaccharide groups, because the carbohydrate moiety has been proved to improve the bioavailability and enhance the receptor-binding affinity of drugs. Anti-diabetic investigation of the synthesized compounds was performed in a zebrafish model using a fluorescently labeled glucose analog 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a glucose tracker. The results indicated that the modification of berberine with carbohydrate groups could give derivatives with improved anti-diabetic activity, in particular the diglucose modified berberine derivative I which could dramatically promote the uptake of 2-NBDG in both zebrafish larvae and their eyes even at very low concentrations Furthermore, the fluorescence-based anti-diabetic investigation method in zebrafish shows great potential for anti-diabetic drug screening. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4HPLC of Formula: 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.HPLC of Formula: 4163-60-4

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics