Tag: 300-400

Sulfonate Version of OHPAS Linker Has Two Distinct Pathways of Breakdown: Elimination Route Allows Para-Hydroxy-Protected Benzylsulfonate (PHP-BS) to Serve as an Alternative Self-Immolative Group was written by Park, Suho;Kim, Sun Young;Cho, Jongun;Jung, Doohwan;Ha, Jihyeon;Seo, Donghoon;Lee, Jaeho;Lee, Sangkwang;Yun, Sanghyeon;Lee, Hyangsook;Park, Okku;Seo, Beomseok;Kim, Sena;Seol, Minah;Song, Jina;Park, Tae Kyo. And the article was included in Bioconjugate Chemistry in 2020.Formula: C16H22O11 This article mentions the following:

Recently we have reported that the ortho-hydroxy-protected aryl sulfate (OHPAS) system can be exploited as a new self-immolative group (SIG) for phenolic payloads. We extended the system to nonphenolic payloads by simply introducing a para-hydroxy benzyl (PHB) spacer. As an addnl. variation of the system, we explored a benzylsulfonate version of the OHPAS system and found that it has two distinct breakdown pathways, cyclization and 1,4-elimination, the latter of which implies that para-hydroxy-protected (PHP) benzylsulfonate (BS) can also be used as an alternative SIG. The PHP-BS system was found to be stable chem. and in mouse and human plasma, having payload release rates comparable to those of the original OHPAS conjugates. 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. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Formula: C16H22O11

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

Anomeric equilibria in derivatives of amino sugars. Nuclear magnetic resonance studies on acetylated amino sugars and specifically deuterated analogs was written by Horton, Derek;Hughes, Jack B.;Jewell, Jon S.;Philips, Kerstin D.;Turner, William Nelson. And the article was included in Journal of Organic Chemistry in 1967.Formula: C16H23NO10 This article mentions the following:

Acetylation of derivatives of 2-amino-2-deoxy-D-glucose and 2-amino-2-deoxy-D-mannose with Ac2O-d6 permitted definitive assignment of the signal for the N-Ac Me group in the N.M.R. spectra of the pyranose pentaacetates of the 2 amino sugars, and some related derivatives The anomeric compositions of the mixtures formed by acetylation of the amino sugars, and a number of simple sugars, with Ac2O in pyridine, were investigated. Aryl substituents in acetylated sugar derivatives are shown to cause shielding of certain Ac groups, with the result that, in CHCl3-d, the N.M.R. signals of these Ac groups are observed at unusually high field. 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: 6730-10-5Formula: C16H23NO10).

(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. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Formula: C16H23NO10

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

On-bead peptoid dimerization induced by incorporation of glycosylated bridging units in submonomer solid-phase approach to glycopeptoids was written by Comegna, Daniela;Del Gatto, Annarita;Saviano, Michele;Zaccaro, Laura. And the article was included in Organic Letters in 2019.Recommanded Product: 4163-60-4 This article mentions the following:

A study on submonomer solid-phase synthesis of S-glycopeptoids has been carried out by screening different parameters. Dimeric species, featuring glycosylated bridging amino monomers, were found under suitable conditions. These dimers arise from an on-resin crosslinking reaction occurring with the incorporation of a glycoamino submonomer into the growing chain and subsequent nucleophilic attack of the resulting secondary amine to a still unreacted bromoacetylated unit. The arising byproduct can be regarded as a novel dimeric peptoid type. 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: 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 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, including apples, durians, pears, bananas, pineapples, and strawberries. 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: 4163-60-4

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

Complexation of hexosammonium ions: evidence for contributions from OH···OH hydrogen bonds in a hydroxylic medium was written by Savage, Paul B.;Gellman, Samuel H.. And the article was included in Journal of the American Chemical Society in 1993.Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate This article mentions the following:

The synthesis and complexation properties of macrocycle 3 (I) are described. Simpler macrocycle 1 (II) was previously shown to bind primary ammonium ions in CDCl₃/CD₃OD mixtures; the authors now report that 3 binds hexosammonium ions in 10 volume% CD₃OD in CDCl₃. The following K_a values were measured for 3 and several hexosamine-HCl as their (p-tert-butylbenzyl)thioglycoside derivatives: β-glucosammonium (3,000 M^-1), α-glucosammonium (2,800 M^-1), β-galactosammonium (1,400 M^-1), β-mannosammonium (1,000 M^-1), α-mannosammonium (2,200 M^-1). Macrocycle 3 binds cyclohexylammonium chloride with a K_a of only 570 M^-1, i.e., significantly less strongly than the hexosammonium ions. In contrast, macrocycle 1 binds cyclohexylammonium chloride more tightly than the hexosammonium ions (e.g., 1,700 M^-1 for 1 + cyclohexylammonium chloride vs. 870 M^-1 for 1 + β-glucosammonium derivative). Thus, interactions between the peripheral hydroxyl groups of macrocycle 3 and the monosaccharide hydroxyls contribute to the stability of the bound state. This observation is particularly interesting in light of the fact that the solvent (2.5 M CD₃OD) contains ample hydroxyl groups for competitive H-bonding interaction. 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: 6730-10-5Application In Synthesis of (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate).

(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 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, including apples, durians, pears, bananas, pineapples, and strawberries. 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 (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

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

Pillar[5]arene-Containing Metallacycles and Host-Guest Interaction Caused Aggregation-Induced Emission Enhancement Platforms was written by Tuo, Wei;Sun, Yan;Lu, Shuai;Li, Xiaopeng;Sun, Yao;Stang, Peter J.. And the article was included in Journal of the American Chemical Society in 2020.Recommanded Product: 4163-60-4 This article mentions the following:

Coordination-driven Pt metallacycles have shown potential in controllable modular self-assembly, which has made a vital contribution to biomedicine, catalysis, and multiresponsive materials. Herein, pillar[5]arene units were integrated into one skeleton through coordination-driven self-assembly, resulting in the formation of a hexagonal Pt(II) metallacycle decorated with six pillar[5]arenes. The host-guest interactions of the as-prepared metallacycle (pillar[5]arenes as hosts) and 1-butyl-4-[4-(diphenylamino)styryl]pyridinium (guest) were investigated. The metallacycle was found to facilitate the coaggregation between the guests and pillar[5]arenes through a synergistic effect, thus engendering a sharp increase in fluorescence intensity. The resultant aggregate was investigated by DLS and TEM. Our studies imply that the pillar[5]arene-containing metallacycle can serve as a potential platform for realizing emission enhancement effects. 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: 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 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.Recommanded Product: 4163-60-4

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

Substrate Specificity Profiling and Identification of a New Class of Inhibitor for the Major Protease of the SARS Coronavirus was written by Goetz, D. H.;Choe, Y.;Hansell, E.;Chen, Y. T.;McDowell, M.;Jonsson, C. B.;Roush, B. C.;McKerrow, J.;Craik, C. S.. And the article was included in Biochemistry in 2007.Synthetic Route of C16H24N2O4 This article mentions the following:

Severe acute respiratory syndrome (SARS) is an emerging infectious disease associated with a high rate of mortality. The SARS-associated coronavirus (SARS-CoV) has been identified as the etiol. agent of the disease. Although public health procedures have been effective in combating the spread of SARS, concern remains about the possibility of a recurrence. Various approaches are being pursued for the development of efficacious therapeutics. One promising approach is to develop small mol. inhibitors of the essential major polyprotein processing protease 3Clpro. Here we report a complete description of the tetrapeptide substrate specificity of 3Clpro using fully degenerate peptide libraries consisting of all 160 000 possible naturally occurring tetrapeptides. The substrate specificity data show the expected P1-Gln P2-Leu specificity and elucidate a novel preference for P1-His containing substrates equal to the expected preference for P1-Gln. These data were then used to develop optimal substrates for a high-throughput screen of a 2000 compound small-mol. inhibitor library consisting of known cysteine protease inhibitor scaffolds. We also report the 1.8 Å X-ray crystal structure of 3Clpro bound to an irreversible inhibitor. This inhibitor, an α,β-epoxyketone, inhibits 3Clpro with a k₃/K_i of 0.002 μM^-1 s^-1 in a mode consistent with the substrate specificity data. Finally, we report the successful rational improvement of this scaffold with second generation inhibitors. These data provide the foundation for a rational small-mol. inhibitor design effort based upon the inhibitor scaffold identified, the crystal structure of the complex, and a more complete understanding of P1-P4 substrate specificity. 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: 87694-53-9Synthetic Route of C16H24N2O4).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) 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. 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.Synthetic Route of C16H24N2O4

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

Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of Pseudomonas aeruginosa was written by Meiers, Joscha;Zahorska, Eva;Roehrig, Teresa;Hauck, Dirk;Wagner, Stefanie;Titz, Alexander. And the article was included in Journal of Medicinal Chemistry in 2020.Synthetic Route of C16H22O11 This article mentions the following:

Chronic infections by Pseudomonas aeruginosa are characterized by biofilm formation, which effectively enhances resistance toward antibiotics. Biofilm-specific antibiotic delivery could locally increase drug concentration to break antimicrobial resistance and reduce the drug’s peripheral side effects. Two extracellular P. aeruginosa lectins, LecA and LecB, are essential structural components for biofilm formation and thus render a possible anchor for biofilm-targeted drug delivery. The standard-of-care drug ciprofloxacin suffers from severe systemic side effects and was therefore chosen for this approach. We synthesized several ciprofloxacin-carbohydrate conjugates and established a structure-activity relationship. Conjugation of ciprofloxacin to lectin probes enabled biofilm accumulation in vitro, reduced the antibiotic’s cytotoxicity, but also reduced its antibiotic activity against planktonic cells due to a reduced cell permeability and on target activity. This work defines the starting point for new biofilm/lectin-targeted drugs to modulate antibiotic properties and ultimately break antimicrobial resistance. 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 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. 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.Synthetic Route of C16H22O11

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

Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding was written by Deng, Hui;Kooijman, Sander;van den Nieuwendijk, Adrianus M. C. H.;Ogasawara, Daisuke;van der Wel, Tom;van Dalen, Floris;Baggelaar, Marc P.;Janssen, Freek J.;van den Berg, Richard J. B. H. N.;den Dulk, Hans;Cravatt, Benjamin F.;Overkleeft, Herman S.;Rensen, Patrick C. N.;van der Stelt, Mario. And the article was included in Journal of Medicinal Chemistry in 2017.Product Details of 87694-53-9 This article mentions the following:

Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoyl glycerol (2-AG) that activates cannabinoid CB₁ receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4-substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5-position of the piperidine ring provided ultrapotent inhibitor I (DH376) with picomolar activity. Compound I temporarily reduces fasting-induced refeeding of mice, thereby emulating the effect of cannabinoid CB₁-receptor inverse agonists. This was mirrored by II (DO34) but also by the neg. control compound III (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple mol. targets. 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: 87694-53-9Product Details of 87694-53-9).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) 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.Product Details of 87694-53-9

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

2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study was written by Morelli, Laura;Legnani, Laura;Ronchi, Silvia;Confalonieri, Laura;Imperio, Daniela;Toma, Lucio;Compostella, Federica. And the article was included in Carbohydrate Research in 2021.SDS of cas: 6730-10-5 This article mentions the following:

The role of the cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose, promoted by BSP/Tf₂O via α-triflate intermediates, has been investigated through a combined computational and exptl. approach. DFT calculations were used to locate the transition states leading to the α or β anomers. These data indicate the preferential formation of the β-adduct with mannosyl donors either equipped with the 4,6-O-benzylidene protection or without it. The synthetic results confirmed this preference, showing in both cases an α/β selectivity of 4:6. This highlights a role for the 2,3-N,O-carbamate in sharp contrast with what described in the case of 2,3-O-carbonate mannosyl donors. 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: 6730-10-5SDS of cas: 6730-10-5).

(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 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.SDS of cas: 6730-10-5

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

Comprehensive insights into the interactions of dicyclohexyl phthalate and its metabolite to human serum albumin was written by Lv, Xiaolan;Jiang, Zheng;Zeng, Guofang;Zhao, Sujuan;Li, Na;Chen, Fengping;Huang, Xiaojian;Yao, Jia;Tuo, Xun. And the article was included in Food and Chemical Toxicology in 2021.Application In Synthesis of Dicyclohexyl phthalate This article mentions the following:

Phthalate esters (PAEs) are a type of persistent organic pollutants and have received widespread concerns due to their adverse effects on human health. Dicyclohexyl phthalate (DCHP) and its metabolite monocyclohexyl phthalate (MCHP) were selected to explore the mechanism for interaction of PAEs with human serum albumin (HSA) through mol. docking and several spectroscopic techniques. The results showed that DCHP/MCHP can spontaneously occupy site I to form a binary complex with HSA, and DCHP exhibited higher binding affinity to HSA than MCHP. At 298 K, the binding constants (K_b) of DCHP and MCHP to HSA were 24.82 x 10⁴ and 1.04 x 10⁴ M^-1, resp. Hydrogen bonds and van der Waals forces were the major driving forces in DCHP/MCHP-HSA complex. The presence of DCHP/MCHP induced the secondary structure changes in HSA, and the pi electrons of the benzene ring skeleton of DCHP/MCHP played a key role in this binding processes. Exposure of DCHP/MCHP to TM4 cells revealed that interactions between PAEs and serum albumin can affect their cytotoxicity; DCHP showed higher toxicity than MCHP. The binding affinity of PAEs with HSA may be a valuable parameter for rapid assessment of their toxicity to organisms. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7Application In Synthesis of Dicyclohexyl phthalate).

Dicyclohexyl phthalate (cas: 84-61-7) 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. 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.Application In Synthesis of Dicyclohexyl phthalate

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