Tag: M.W=150-200

Jia, Yong published the artcileAn aldo-keto reductase with 2-keto-L-gulonate reductase activity functions in L-tartaric acid biosynthesis from vitamin C in Vitis vinifera, Formula: C6H10O7, the publication is Journal of Biological Chemistry (2019), 294(44), 15932-15946, database is CAplus and MEDLINE.

Tartaric acid has high economic value as an antioxidant and flavorant in food and wine industries. L-Tartaric acid biosynthesis in wine grape (Vitis vinifera) uses ascorbic acid (vitamin C) as precursor, representing an unusual metabolic fate for ascorbic acid degradation Reduction of the ascorbate breakdown product 2-keto-L-gulonic acid to L-idonic acid constitutes a critical step in this L-tartaric acid biosynthetic pathway. However, the underlying enzymic mechanisms remain obscure. Here, we identified a V. vinifera aldo-keto reductase, Vv2KGR, with 2-keto-L-gulonic acid reductase activity. Vv2KGR belongs to the D-isomer-specific 2-hydroxyacid dehydrogenase superfamily and displayed the highest similarity to the hydroxyl pyruvate reductase isoform 2 in Arabidopsis thaliana. Enzymic analyses revealed that Vv2KGR efficiently reduces 2-keto-L-gulonic acid to L-idonic acid and uses NADPH as preferred coenzyme. Moreover, Vv2KGR exhibited broad substrate specificity toward glyoxylate, pyruvate, and hydroxypyruvate, having the highest catalytic efficiency for glyoxylate. We further determined the X-ray crystal structure of Vv2KGR at 1.58 Å resolution Comparison of the Vv2KGR structure with those of D-isomer-specific 2-hydroxyacid dehydrogenases from animals and microorganisms revealed several unique structural features of this plant hydroxyl pyruvate reductase. Substrate structural anal. indicated that Vv2KGR uses two modes (A and B) to bind different substrates. 2-Keto-L-gulonic acid displayed the lowest predicted free-energy binding to Vv2KGR among all docked substrates. Hence, we propose that Vv2KGR functions in L-tartaric acid biosynthesis. To the best of our knowledge, this is the first report of a D-isomer-specific 2-hydroxyacid dehydrogenase that reduces 2-keto-L-gulonic acid to L-idonic acid in plants.

Journal of Biological Chemistry published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Formula: C6H10O7.

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

Jirasek, Fabian published the artcileSolid-liquid equilibrium in the system 2-keto-L-gulonic acid + sodium-2-keto-L-gulonate + water, Application of (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, the publication is Fluid Phase Equilibria (2018), 318-322, database is CAplus.

The solid-liquid equilibrium (SLE) in the ternary system 2-keto-L-gulonic acid (HKGA) + sodium-2-keto-L-gulonate (NaKGA) + water was studied exptl. at temperatures between 275 and 313 K and ambient pressure. At these conditions, HKGA and NaKGA precipitate as monohydrates: HKGA·H₂O and NaKGA·H₂O, resp. Phase diagrams with one eutonic point are found for all temperatures A thermodn. model of the SLE that is based on an extended version of the Debye-Huckel theory was developed and the dissociation constant of HKGA as well as the solubility products of HKGA·H₂O and NaKGA·H₂O were determined The agreement between the exptl. data and the results from the model is excellent.

Fluid Phase Equilibria published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C6H10O7, Application of (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid.

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

Al Sulaiman, Dana published the artcileChemically Modified Hydrogel-Filled Nanopores: A Tunable Platform for Single-Molecule Sensing, Application In Synthesis of 6346-09-4, the publication is Nano Letters (2018), 18(9), 6084-6093, database is CAplus and MEDLINE.

Label-free, single-mol. sensing is an ideal candidate for biomedical applications that rely on the detection of low copy numbers in small volumes and potentially complex biofluids. Among them, solid-state nanopores can be engineered to detect single mols. of charged analytes when they are elec. driven through the nanometer-sized aperture. When successfully applied to nucleic acid sensing, fast transport in the range of 10-100 nucleotides per ns often precludes the use of standard nanopores for the detection of the smallest fragments. Herein, hydrogel-filled nanopores (HFN) are reported that combine quartz nanopipettes with biocompatible chem. poly(vinyl) alc. hydrogels engineered inhouse. Hydrogels were modified phys. or chem. to finely tune, in a predictable manner, the transport of specific mols. Controlling the hydrogel mesh size and chem. composition allowed us to slow DNA transport by 4 orders of magnitude and to detect fragments as small as 100 base pairs (bp) with nanopores larger than 20 nm at an ionic strength comparable to physiol. conditions. Considering the emergence of cell-free nucleic acids as blood biomarkers for cancer diagnostics or prenatal testing, the successful sensing and size profiling of DNA fragments ranging from 100 bp to >1 kbp long under physiol. conditions demonstrates the potential of HFNs as a new generation of powerful and easily tunable mol. diagnostics tools.

Nano Letters published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C8H19NO2, Application In Synthesis of 6346-09-4.

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

Vidaluc, Jean-Louis published the artcileFlexible 1-[(2-Aminoethoxy)alkyl]-3-ar(o)yl(thio)ureas as Novel Acetylcholinesterase Inhibitors. Synthesis and Biochemical Evaluation, Synthetic Route of 101-98-4, the publication is Journal of Medicinal Chemistry (1995), 38(15), 2969-73, database is CAplus and MEDLINE.

A series of flexible 1-(2-aminoethoxy)-3-ar(o)yl(thio)ureas was synthesized and assessed for antiacetylcholinesterase activity. This series was designed in order to optimize the spacer length linking the two pharmacophoric moieties, i.e., the basic nitrogen and the ar(o)yl(thio)urea unit, and to test compounds with greater conformational flexibility. Thus, the replacement of the previously described spacer, 4-piperidinylethyl, by a linear ethoxyethyl chain gave compounds of slightly comparable potency, providing that they were correctly substituted. The results show that this new flexible spacer is compatible with high inhibitory activities. The optimal chain length corresponds to five methylene groups, allowing an efficient interaction between the two pharmacophoric units and the two reported hypothetical enzyme hydrophobic binding sites. Moreover, the initially optimized benzyl group, attached to the basic nitrogen, was found to be advantageously replaced by a cyclohexyl group, showing that an aromatic residue does not represent a prerequisite for activity.

Journal of Medicinal Chemistry published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C15H24O2, Synthetic Route of 101-98-4.

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

Poupart, Marc-Andre published the artcileSolid-Phase Synthesis of Peptidomimetic Inhibitors for the Hepatitis C Virus NS3 Protease, Quality Control of 27292-49-5, the publication is Journal of Organic Chemistry (2001), 66(14), 4743-4751, database is CAplus and MEDLINE.

The NS3 serine protease enzyme of the hepatitis C virus (HCV) is essential for viral replication. Short peptides mimicking the N-terminal substrate cleavage products of the NS3 protease are known to act as weak inhibitors of the enzyme and have been used as templates for the design of peptidomimetic inhibitors. Automated solid-phase synthesis of a small library of compounds based on such a peptidomimetic scaffold has led to the identification of potent and highly selective inhibitors of the NS3 protease enzyme.

Journal of Organic Chemistry published new progress about 27292-49-5. 27292-49-5 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Benzene,Phenol, name is 3-Morpholinophenol, and the molecular formula is C10H13NO2, Quality Control of 27292-49-5.

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

Achour, Mariem published the artcileBioavailability and nutrikinetics of rosemary tea phenolic compounds in humans, HPLC of Formula: 621-37-4, the publication is Food Research International (2021), 109815, database is CAplus and MEDLINE.

Rosmarinus officinalis L. is a widespread aromatic plant commonly consumed as a tea in traditional cuisine and in folk medicine to treat various illnesses due to its therapeutic properties. To the best of our knowledge, there are no reports on the bioavailability and metabolism of R. officinalis tea polyphenols in humans. This study was aimed at assessing the bioavailability and nutrikinetics of R. officinalis phenolic compounds in healthy humans for the first time. Forty-eight compounds were identified in plasma and urine. Few un-metabolized compounds were detected since rosemary polyphenols were extensively metabolized into phase II conjugates, with rapid appearance and clearance in plasma, pointing to small intestinal absorption. Phase II derivatives of caffeic acid showed kinetics compatible with both intestinal and colonic hydrolysis of rosmarinic acid yielding free caffeic and 3,4-dihydroxyphenyl-lactic acids, which were absorbed and metabolized into phase II derivatives These metabolites, along with reduced forms of caffeic acid and their phase II metabolites, and those of hydroxyphenylpropionic, hydroxylphenylacetic, benzoic and hippuric acids, highlight the importance of colonic absorption. Total urinary excretion of the phenols added up to 235 μmol, corresponding to 22.3% of the ingested amount (1055 μM). In conclusion, rosemary tea polyphenols are partially bioavailable and extensively metabolized, mainly by the colonic microbiota.

Food Research International published new progress about 621-37-4. 621-37-4 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Phenol,Natural product, name is 3-Hydroxyphenylacetic acid, and the molecular formula is C8H8O3, HPLC of Formula: 621-37-4.

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

Strunskaya, E. I. published the artcileSynthesis of aryloxy-substituted 1,2,5-thiadiazoles by the Ullmann reaction, Formula: C6H9N3O2S, the publication is Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) (2001), 37(9), 1330-1334, database is CAplus.

3-Aryloxy-1,2,5-thiadiazoles were synthesized by the Ullmann reaction either from 3-chloro-1,2,5-thiadiazoles and phenols having donor substituents or from 3-hydroxy-1,2,5-thiadiazoles and chlorobenzenes containing acceptor substituents.

Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii) published new progress about 30165-97-0. 30165-97-0 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Thiadiazole,Alcohol, name is 4-Morpholino-1,2,5-thiadiazol-3-ol, and the molecular formula is C10H14N2O, Formula: C6H9N3O2S.

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

Mariella, R. P. published the artcileNovel SNl displacement. Reaction of tertiary amines with acetic anhydride, Computed Properties of 101-98-4, the publication is Canadian Journal of Chemistry (1971), 49(20), 3348-51, database is CAplus.

The action of Ac2O on tertiary amines at reflux may cause the displacement of one of the R groups from the amine. The groups which are displaced are benzyl, tert-Bu, benzhydryl, trityl, and cinnamyl; the groups which are not displaced are Me, Et, Bu, Ph, α-naphthyl, iso-Pr, allyl, and propargyl, An SN 1 mechanism with special steric requirements is consistent with the results.

Canadian Journal of Chemistry published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Computed Properties of 101-98-4.

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

Chapman, Eli published the artcileMechanistic studies of β-arylsulfotransferase IV, Quality Control of 120103-18-6, the publication is Proceedings of the National Academy of Sciences of the United States of America (2003), 100(3), 910-915, database is CAplus and MEDLINE.

Sulfotransferases are an important class of enzymes that catalyze the transfer of a sulfuryl group to a hydroxyl or amine moiety on various mols. including small-mol. drugs, steroids, hormones, carbohydrates, and proteins. They have been implicated in a number of disease states but remain poorly understood, complicating the design of specific, small-mol. inhibitors. A linear free-energy anal. in both the forward and reverse directions indicates that the transfer of a sulfuryl group to an aryl hydroxyl group catalyzed by β-arylsulfotransferase IV likely proceeds by a dissociative (sulfotrioxide-like) mechanism. Values for the Bronsted coefficients (β_nuc and β_lg) are +0.33 and -0.45, giving Leffler α values of 0.19 and 0.61 for the forward and reverse reactions, resp.

Proceedings of the National Academy of Sciences of the United States of America published new progress about 120103-18-6. 120103-18-6 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Nitro Compound,Benzene,Phenol, name is 2,5-Difluoro-4-nitrophenol, and the molecular formula is C6H3F2NO3, Quality Control of 120103-18-6.

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

King, Sandra M. published the artcileDevelopment of a method for the N-arylation of amino acid esters with aryl triflates, Application of 4-(1H-Pyrrol-1-yl)phenol, the publication is Organic Letters (2016), 18(16), 4128-4131, database is CAplus and MEDLINE.

A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including Me, tert-Bu, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experiment (DOE) anal. using JMP software. The mild reaction conditions, which use t-BuBrettPhos Pd G3 or G4 precatalyst, result in minimal racemization of the amino acid ester. This method is the first synthetic application of the t-BuBrettPhos Pd G4 precatalyst. Mechanistic studies show that the observed erosion in enantiomeric excess is due to racemization of the amino acid ester starting material and not of the product.

Organic Letters published new progress about 23351-09-9. 23351-09-9 belongs to alcohols-buliding-blocks, auxiliary class Pyrrole,Benzene,Alcohol, name is 4-(1H-Pyrrol-1-yl)phenol, and the molecular formula is C10H9NO, Application of 4-(1H-Pyrrol-1-yl)phenol.

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