Extracurricular laboratory:new discovery of H-D-Pro-OH

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Reference of 344-25-2, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.344-25-2, Name is H-D-Pro-OH, molecular formula is C5H9NO2. In a Patent,once mentioned of 344-25-2

Compounds of the formulaare disclosed. The compounds are CCR1 antagonists which are useful for the treatment and prevention of inflammatory and autoimmune diseases. Other embodiments are also disclosed.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

A new application about H-D-Pro-OH

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This invention is directed to pyrrole, pyrazole, imidazole, triazole, and morpholine based selective androgen receptor degrader (SARD) compounds including heterocyclic anilide rings and their synthetic precursors, R-isomers, and non-hydroxylated and/or non-chiral propanamides, and pharmaceutical compositions and uses thereof in treating prostate cancer, advanced prostate cancer, castration resistant prostate cancer, triple negative breast cancer, other cancers expressing the androgen receptor, androgenic alopecia or other hyperandrogenic dermal diseases, Kennedy’s disease, amyotrophic lateral sclerosis (ALS), abdominal aortic aneurysm (AAA), and uterine fibroids, and to methods for reducing the levels of androgen receptor-full length (AR-FL) including pathogenic or resistance mutations, AR-splice variants (AR-SV), and pathogenic polyglutamine (polyQ) polymorphisms of AR in a subject.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Three new chiral stationary phases (CSPs) for high-performance liquid chromatography were prepared from R-(3,3′-halogen substituted-1,1′-binaphthyl)-20-crown-6 (halogen = Cl, Br and I). The experimental results showed that R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 (CSP-1) possesses more prominent enantioselectivity than the two other halogen-substituted crown ether derivatives. All twenty-one alpha-amino acids have different degrees of separation on R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6-based CSP-1 at room temperature. The enantioselectivity of CSP-1 is also better than those of some commercial R-(1,1′-binaphthyl)-20-crown-6 derivatives. Both the separation factors (alpha) and the resolution (Rs) are better than those of commercial crown ether-based CSPs [CROWNPAK CR(+) from Daicel] under the same conditions for asparagine, threonine, proline, arginine, serine, histidine and valine, which cannot be separated by commercial CR(+). This study proves the commercial usefulness of the R-(3,3′-dibromo-1,1′-binaphthyl)-20-crown-6 chiral stationary phase.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Phosphonamidates which bear a simple resemblance to penicillin type structures have been synthesised as potential inhibitors of beta-lactamases: -ethyl N-(benzyloxycarbonyl) amidomethyl phosphonyl amides, PhCH2OCONHCH2P(O)(OEt)NR2, the amines HNR2 being L-proline, D-proline, L-thiazolidine, and o-anthranilic acid. The proline derivatives completely and irreversibly inactivated the class C beta-lactamase from Enterobacter cloacae P99, in a time-dependent manner, indicative of covalent inhibition. The inactivation was found to be exclusive to the class C enzyme and no significant inhibition was observed with any other class of beta-lactamase. The anthranilic acid derivative exhibited no appreciable inactivation of the beta-lactamases. The phosphonyl proline and phosphonyl thioproline derivatives were separated into their diastereoisomers and their individual second order rate constants for inhibition were found to be 7.72 ± 0.37 and 8.3 × 10-2 ± 0.004 M-1 s-1 for the L-proline derivatives, at pH 7.0. The products of the inhibition reaction of each individual diastereoisomer, analyzed by electrospray mass spectroscopy, indicate that the more reactive diastereoisomers phosphonylate the enzyme by P-N bond fission with the elimination of proline. Conversely, gas chromatographic detection of ethanol release by the less reactive proline diastereoisomer suggests phosphonylation occurs by P-O bond fission. The enzyme enhances the rate of phosphonylation with P-N fission by at least 106 compared with that effected by hydroxide-ion. The pH dependence of the rate of inhibition of the beta-lactamase by the more reactive diasteroisomer is consistent with the reaction of the diprotonated form of the enzyme, EH2, with the inhibitor, I (or its kinetic equivalents EH with IH). This pH dependence and the rate enhancement indicate that the enzyme appears to use the same catalytic apparatus for phosphonylation as that used for hydrolysis of beta-lactams. The stereochemical consequences of nucleophilic displacement at the phosphonyl centre are discussed.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Extended knowledge of H-D-Pro-OH

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about is helpful to your research. category: catalyst-ligand

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We have realized that N-formylations of free amines of some drug leads can improve PK/PD property of parent molecules without decreasing their biological activities. In order to selectively formylate primary amines of polyfunctional molecules, we have sought a mild and convenient formylation reaction. In our screening of N-formylation of an alpha-amino acid, l-phenylalanine, none of formylation conditions reported to date yielded the desired HCO-l-Phe-OH with satisfactory yield. N-formylations of amino acids with HCO2H require a water-containing media and suppress polymerization reactions due to the competitive reactions among carboxylic acids. We found that N-formylations of alpha-amino acids could be achieved with a water-soluble peptide coupling additive, an Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-cyano-2- (hydroxyimino)acetate (2), EDCI, and NaHCO3 in water or a mixture of water and DMF system, yielding N-formylated alpha-amino acids with excellent yields. Moreover, these conditions could selectively formylate primary amines over secondary amines at a controlled temperature. A usefulness of these conditions was demonstrated by selective formylation of daptomycin antibiotic which contains three different amino groups.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

New explortion of H-D-Pro-OH

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Dopamine agonist compounds disclosed are useful in treating hypertension and congestive heart failure in mammals. The compounds have the following general formula (I) STR1 wherein: X is nitrogen or CH;

R is hydrogen or lower alkyl;

R 1, R’ 1, R 2, R’ 2, R 3, R’ 3, R 4, R’ 4, R 5 and R’ 5 are each independently hydrogen, STR2 respectively represent–(CH 2) n–and (CH 2) m wherein n and m are each independently an integer of from 1 to 10 and pharmaceutically acceptable salts, S stereoisomers and racemic and non-racemic mixtures thereof.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Phytoconstituents are non-nutrient active plant chemical compounds or bioactive compounds and are responsible for protecting the plant against infections, infestations, or predation by microbes, pests, pathogens, or predators. Some are responsible for color, aroma, and other organoleptic properties. Phytoconstituents are synthesized in plants through primary and secondary metabolic pathways and many of them may be grouped as active drug constituents and inert nondrug constituents. A wide range of active components has been discovered and they have been divided into 16 main or more groups and the most important of them are alkaloids, terpenoids, phenols and phenolic glycosides, coumarins and their glycosides, anthraquinones and their glycosides, flavones and flavonoid glycosides or heterosides, mucilage and gums, tannins, volatile oils, saponins, cardioactive glycosides, cyanogenic glycosides, etc. Other relevant active constituents in plants, such as vitamins, minerals, amino acids, carbohydrates and fibers, some sugars, organic acids, lipids, and antibiotics, are essential nutrients. In addition to other functions, secondary metabolites produced in plants are used for communication as signal compounds to attract different pollinating agents including insects (honey bees, bumble bees, moths), birds, lizards, bats, etc. Classification of phytochemicals may be made based on their elemental constituents such as C & H; C, H & O; C, H, O, N, S & P containing compounds, O/N containing heterocyclic compounds, and other miscellaneous compounds. Some of these may be grouped as primary and others as secondary metabolites. Primary metabolic products consisting of C & H; C, H & O; N, S & P elements include hydrocarbons, carbohydrates, lipids, amino acids, proteins, nucleic acids, organic acids, etc. Genetic effects and environmental factors exert both qualitative and quantitative alterations of the active constituents in medicinal plants.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

More research is needed about H-D-Pro-OH

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“Collaboration” is not the first word most would associate with the field of total synthesis. In fact, the spirit of total synthesis is all-too-often reputed as being more competitive, rather than collaborative, sometimes even within individual laboratories. However, recent studies in total synthesis have inspired a number of collaborative efforts that strategically blend synthetic methodology, biocatalysis, biosynthesis, computational chemistry, and drug discovery with complex molecule synthesis. This Perspective highlights select recent advances in these areas, including collaborative syntheses of chlorolissoclimide, nigelladine A, artemisinin, ingenol, hippolachnin A, communesin A, and citrinalin B. The legendary Woodward-Eschenmoser collaboration that led to the total synthesis of vitamin B12 is also discussed.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Can You Really Do Chemisty Experiments About 344-25-2

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Asymmetric oxidative coupling of (S)-1-(3-hydroxy-2-naphthylcarbonyl)pyrrolidine-2-carboxylic acid methyl ester 1 catalyzed by CuCl afforded (S,S,R)-2,2?-dihydroxy-3,3?-bis(2-methoxycarbonyl-1- pyrrolidinylcarbonyl)-1,1?-binapthalene 2 with diastereomeric excess up to 65.9%. (R)-BINOL-3,3?-diacid 3 was obtained in 30% overall yield and 97% e.e. by separating the diastereomers and hydrolyzing 2.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The application relates to optically active compounds of the general formula (I): Formula (I) wherein R means a hydrogen atom or a straight or branched alkyl group containing 1-4 carbon atoms, R1 means a hydrogen atom or a straight or branched alkyi group containing 1-4 carbon atoms, R2 means a hydrogen atom or a straight or branched alkyl group containing 1-4 carbon atoms- and their salts. Compounds of the general formula (I) are useful intermediates of the therapeutically active compounds described in US-6673790 and in J. Pharmacol. Exp. Ther. 309 p 414 (2004).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI