Glycine Methyl Ester Hydrochloride Research Articles

Synthesis, Growth, Photoluminescence, Thermal, and Third-Order Nonlinear Optical Properties of Glycine Methyl Ester Hydrochloride Single Crystal for Opto-Electronic Applications

Synthesis, Growth, Photoluminescence, Thermal, and Third-Order Nonlinear Optical Properties of Glycine Methyl Ester Hydrochloride Single Crystal for Opto-Electronic Applications

Growth, structural, spectroscopic, DFT calculations, insilico biological analysis of glycine methyl ester hydrochloride (GMEHCl) against human estrogen receptor

On Glycine Methyl Ester Hydrochloride (GMEHCl), X-ray crystallographic (Lattice parameter), FT-IR, FT-Raman, DFT, HOMO-LUMO, MEP, ADMET, and molecular docking investigations are studied. The small molecule (GMEHCl) docking analysis with the target protein revealed that this is a good molecule that docks well with a target connected to the Human estrogen receptor macromolecule. The improvement of electrostatic interactions between the protein and the ligand is made possible by molecular electrostatic potential (MEP). DFT-B3LYP calculations using the 6–31++G (d,p) basis set are used to determine the optimized geometry of the GMEHCl molecule, and the computed vibrational frequencies are assessed by comparing them to experimental results. Using a 2D fingerprint plot and Hirshfeld Surfaces, the molecular surface and hydrogen bonding interactions in the GMEHCl crystal structure were discovered and investigated. The parameters of absorption, distribution, metabolism, and excretion (ADME) were measured using the internet server preADMET.

19 Molecular Docking Analysis of Volatile Compounds from Fraction of Eichhornia crassipes Herbs Ethanol Extract As α-Glucosidase Inhibitor

Diabetes mellitus is a degenerative disease characterized by an increase in blood sugar (hyperglycemia).Inhibiting it will prevent the uptake of glucose in the plasma. One of the plants that can be usedas antidiabetic is E. crassipes herbs. This research aims to know the interaction between volatilechemical compounds from ethyl acetate fraction and ethanol fraction of ethanol extract of E. crassipesherbs with the α-glucosidase enzyme. This study used ethanol extract of E. crassipes herbs with avariation of ethyl acetate fraction and ethanol fraction then analyzed the fraction using GC-MS (GasChromatography-Mass Spectroscopy). The ethyl acetate fraction contained 2-pyridine-propanoicacid, alpha.-methyl-.beta.-oxo-,Ethyl ester;1-propanol-1-di; carbamic acid, methyl ester; acetic acid,aminooxy-, hydrazide; (2R) - [2-2H2] glycine methyl ester hydrochloride. The ethanol fractioncontained semicarbazide hydrochloride; carbonic dihydrazide; hydroxy-acetaldehyde; 1-propanol-1-di; acetic acid, and hydroxyl. The result of docking with the α-glucosidase enzyme is 2-pyridinepropanoicacid, alpha.-methyl-.beta.-oxo-, the Ethyl ester of the ethyl acetate fraction having ΔG is-4.14 Kcal/mol. Semicarbazide hydrochloride from the ethanol fraction has ΔG of -3.17 Kcal/mol.Keywords: Diabetes mellitus, docking molecular, (Eichhornia crassipes (Mart.) Solms Herbs, ethylacetate fraction, α-glucosidase enzyme.

Improving the performance of water-based drilling fluid using amino acid-modified graphene oxide nanocomposite as a promising additive

It is possible to take advantage of nanomaterials' properties to improve water-based drilling fluids' flux and physical properties. In this paper, glycine methyl ester hydrochloride was synthesized, and the chemical structure was verified to be used as a surface modifier of graphene oxide. At the same time, graphene oxide was prepared from graphite and chlorinated with thionyl chloride, and a nucleophilic substitution reaction was performed to increase the hydrophilicity of graphene oxide. FTIR, Raman, HRTEM, and XRD techniques have identified the prepared and obtained materials from chlorinated graphene oxide's reaction with glycine methyl ester hydrochloride. The glycine-modified graphene oxide (GO) was evaluated as drilling-fluid additives at different concentrations (2.66%, 5.32%, and 10.64%) to enhancement the thermal stability of water-based drilling fluid and reducing the filtration loss. The obtained results confirmed that the successful glycine-modified graphene oxide/bentonite to enhance both thermal stability (up to 350 °F) and filtration loss.

Novel skin permeation enhancers based on amino acid ester ionic liquid: Design and permeation mechanism

This study developed novel ionic liquids (ILs) based on amino acids. We first screened 15 methyl amino acid ester hydrochlorides ([AAC1]Cl) for their skin permeation enhancements using 5-Fluorouracil (5-Fu) and Hydrocortisone (HC) as model drugs. Glycine methyl ester hydrochloride ([GlyC1]Cl), L-proline methyl ester hydrochloride ([L-ProC1]Cl), and L-leucine methyl ester hydrochloride ([L-LeuC1]Cl) were selected, and their ester sites were modified with different carbon chains (C8 and C12). The resulting ILs showed improved permeation to the two drugs. TEWL and CLSM assays revealed the moderation effects of the modified ILs on skin barrier function, whereas L-proline dodecyl ester hydrochloride ([ProC12]Cl) and L-leucine dodecyl ester hydrochloride ([L-LeuC12]Cl) exhibited the strongest activities. Permeation mechanisms were further investigated by ATR-FTIR, solid-NMR, SEM, and TEM analyses. The results suggested that [L-ProC12]Cl and [L-LeuC12]Cl combined the advantages of amino acid esters and IL solvent and could interact with the intercellular lipid domain by the multi-functions of lipid fluidization and lipid extraction, which were observed in a dosage- and time-dependent manner. Additionally, pathological examination suggested that the amino acid ester-based ILs (AAE-ILs) had good biocompatibility. In conclusion, this study has generated novel chemical penetration enhancers (CPEs) based on AAE-ILs and may be potentially utilized in drug transdermal delivery systems (TDDSs).

The investigation of thermosensitive properties of phosphazene derivatives bearing amino acid ester groups

In this study, a series of phosphazene derivatives having amino acid esters were synthesized from the reactions of amino acid esters with cyclophosphazenes. Hexachlorocyclotriphosphazene, (N3P3Cl6) and octachlorocyclotetraphosphazene (N4P4Cl8) have been reacted with carboxylic amino acid esters; glycine ethyl ester hydrochloride, glycine methyl ester hydrochloride, β-alanine ethyl ester hydrochloride, β-alanine methyl ester hydrochloride and methyl 6-aminohexanoate hydrochloride to obtain cyclophosphazene compounds containing amino acid esters as side groups. All obtained compounds (1–9) were characterized using spectroscopic methods and elemental analysis. The molecular structures of compounds 2, 5 and 6 were also characterized by X-ray crystallographic studies. Hydrolytic degradations of compounds (1–9) were observed by 31P NMR spectroscopy under acidic condition (pH = 1–3) and at body temperature (35–38 °C). Concentration-dependent lower critical solution temperatures (LCST) of compounds were examined to determine their thermosensitive behaviors in aqueous solution. It is found that all compounds degraded to harmless products such as amino acid, phosphates, ammonium salts. LCSTs of compounds 1, 2 and 6 were found to be around body temperature that is important for biomedical applications.

Chemical synthesis of the 3-sulfooxy-7- N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1

The chemical synthesis of 3β,7β-dihydroxy-5-cholen-24-oic acid, triply conjugated by sulfuric acid at C-3, by N-acetylglucosamine (GlcNAc) at C-7, and by glycine or taurine at C-24, is described. These are unusual, major metabolites of bile acid found to be excreted in the urine of a patient with Niemann-Pick disease type C1. Analogous double-conjugates of 3β-hydroxy-7-oxo-5-cholen-24-oic acid were also prepared. The principal reactions involved were: (1) β- d- N-acetylglucosaminidation at C-7 of methyl 3β- tert-butyldimethylsilyloxy (TBDMSi)-7β-hydroxy-5-cholen-24-oate with 2-acetamido-1α-chloro-1,2-dideoxy-3,4,6-tri- O-acetyl- d-glucopyranose in the presence of CdCO 3 in boiling toluene; (2) sulfation at C-3 of the resulting 3β-TBDMSi-7β-GlcNAc with sulfur trioxide-trimethylamine complex in pyridine; and (3) direct amidation at C-24 of the 3β-sulfooxy-7β-GlcNAc conjugate with glycine methyl ester hydrochloride (or taurine) using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as a coupling agent in DMF. The structures of the multi-conjugated bile acids were characterized by liquid chromatography-mass spectrometry with an electrospray ionization probe under the positive and negative ionization modes.

Synthesis and Ring‐Opening Metathesis Polymerization (ROMP) Reactivity of endo‐and exo‐Norbornenylazlactone Using Ruthenium Catalysts

AbstractSummary: Norbornenylazlactone (NBAz) was prepared by a Diels‐Alder cycloaddition between cyclopentadiene and 2‐vinyl‐4,4‐dimethyl‐5‐oxazolone. The stereoselectivity of this pericyclic reaction was in favour of endo isomers. The ring‐opening metathesis polymerization (ROMP) of NBAz was carried out in presence of ruthenium catalysts [(PCy3)2(Cl)2RuCHPh 1; (SIMes)(PCy3)(Cl)2RuCHPh 2 (SIMes: 1,3‐dimesityl‐4,5‐dihydroimidazol‐2‐ylidene); (PiPr3)2(Cl)2RuCHSPh 3; (PiPr3)(Cl)2RuCH(CH2)2C, N‐2‐C5H4N 4]. It was found that the exo isomer is much more reactive than the corresponding endo isomer. Some hypotheses of mechanism are suggested to justify the low polymerization rate of endo isomer using the results of NBAz derivatives as the hydrolyzed NBAz, 5, and the coupling product between NBAz and glycine methyl ester hydrochloride, 6. For exo‐NBAz, the propagating rate constant, kp, was determined with the four Ru‐initiators and their activity decreases in the order 2 > 1 > 3 > 4. Complementary kinetic measurements with 1 and 2 were given as kp/ki ratio. The ROMP of exo isomer was faster with 2 than 1 in spite of a worse control of the chains size. The azlactone ring survived intact during the polymerization and may be used for further reactions with nucleophiles.ROMP of NBAz by ruthenium initiators.magnified imageROMP of NBAz by ruthenium initiators.

Simplified Synthesis of Amphiphilic Siloxanes with Methyl Gluconyl Glycinate Functionalities via Transacetalation

New carbohydrate-functional siloxanes (CHFS) have successfully been synthesized by acid-catalyzed transacetalation between unprotected methyl gluconyl glycinate (MGG) as a hydrophilic component and an acetal-functional siloxane in DMF/dioxane mixed solvents. MGG, which can be regarded as a hybrid material composed of a saccharide and an amino acid, was easily synthesized in good yield by amide bond formation between d-glucono-1,5-lactone and glycine methylester hydrochloride. It was demonstrated that both amide and ester groups remained inactive under the transacetalation conditions. A rake-type CHFS as well as an ABA-type CHFS was obtained without an insolubilization problem indicating that the use of this modified carbohydrate is very advantageous in terms of the structural versatility. The materials thus obtained were soluble in both nonpolar solvents such as chloroform and polar solvents such as DMF and DMSO. The hydrophilicity of MGG, glucose, and poly(ethylene oxide) was estimated by the solubility parameter values and compared with the water solubility data. A simple emulsification study of CHFS suggested that these new materials are worth being investigated deeply to find applications, especially personal care and healthcare applications.

Synthesis and transformations of methyl (Z)-2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)propenoate

Methyl (Z)-2-((tert-butoxycarbonyl)amino)-3-(dimethylamino)propenoate (3) was prepared in 2 steps from glycine methyl ester hydrochloride (1). Acid catalysed reactions of 3 with various alkyl-, aryl-, and heteroarylamines 4a-g, performed at 20-80 °C, proceeded by substitution of the dimethylamino group giving the corresponding substitution products, 3-N-substituted methyl (Z)-2-((tert-butoxycarbonyl)-amino)amino)propenoates 5a-g. Treatment of 3 with ambident 1,3- nucleophiles, such as 2-pyridineacetonitrile (6), 2-aminothiazole (4d), 2-aminopyridine (4f), and 4-hydroxy-6-methyl-2H-pyran-3-one (7) in acetic acid at 85-120 °C afforded fused pyridones 8 and 12, pyrimidones 9 and 10 and pyranones 11 and 13.

Synthesis of Some Novel Benzylidenehydantoins: Amino Acids Derivatives

5-Benzylidenehydantoin reacts with chlorosulfonic acid to give the corresponding p-sulfonyl chloride. Condensation of the latter with amino acids leads to sulfonylamino acid derivatives, which on coupling with glycine methyl ester hydrochloride in THF-Et3N using the dicyclohexylcarbodiimide method furnish the desired dipeptide methyl esters. The spectral data of the compounds are briefly discussed.

Greatly Simplified Procedures for the Synthesis of alpha-Amino Acids by the Direct Alkylation of Pseudoephedrine Glycinamide Hydrate.

A modified procedure for the synthesis of highly enantiomerically enriched alpha-amino acids is described that involves the direct alkylation of pseudoephedrine glycinamide hydrate (1.H(2)O) followed by hydrolysis. The modified procedure was developed to overcome several inconvenient aspects of our earlier reported procedure. Advantages of the new method include (1) a greatly simplified one-step synthesis of the alkylation substrate (1.H(2)O) by the direct combination of glycine methyl ester hydrochloride with pseudoephedrine in the presence of lithium tert-butoxide, (2) the use of the weaker base lithium hexamethyldisilazide (LHMDS) in lieu of lithium diisopropylamide (LDA) for the enolization reaction, (3) a protocol for the direct alkylation of 1.H(2)O without the need for prior drying of the alkylation substrate, and (4) a one-step alkylation procedure that generates LHMDS and anhydrous lithium chloride simultaneously from the reaction of lithium metal with n-hexyl chloride in the presence of hexamethyldisilazane.

Solid-Phase Synthesis of 1,4-Benzodiazepine-2,5-diones. Library Preparation and Demonstration of Synthesis Generality

A general and expedient method has been developed for the solid-phase synthesis of 1,4-benzodiazepine-2,5-diones 1 from three commercially available components; anthranilic acids, α-amino esters, and alkylating agents. Reaction conditions have been developed to prepare either racemic compounds for lead identification efforts or optically pure compounds for lead optimization efforts. The incorporation of diverse functionality into the benzodiazepine products has also been demonstrated. On the basis of the scope and generality of the synthesis sequence, a library of 1,4-benzodiazepine-2,5-diones has been prepared from 11 alkylating agents, 12 anthranilic acids, and 19 α-amino esters (nine sets of enantiomeric pairs and glycine methyl ester hydrochloride). The library was prepared in a spatially separate format using a microtiter-based apparatus that is inexpensive and straightforward to construct from ordinary items found in an organic or bioorganic laboratory. The high quality of the 1,4-benzodiazepine-2,5-dione library has been demonstrated by evaluating representative compounds by HPLC analysis and 1H NMR.

Membrane potentials in charged membranes separating solutions of weak electrolytes

M. Kawaguchi, T. Murata and A. Tanioka, J. Chem. Soc., Faraday Trans., 1997, 93, 1351 DOI: 10.1039/A606007B

Synthesis, X-ray structure and alkali-metal binding properties of a new hexahomotriazacalix[3]arene

Hexahomotriazacalix [3] arene 1 has been synthesized by the reaction of 2,6-bis(chloromethyl)-4-methylphenol 6 with glycine methyl ester hydrochloride under high-dilution conditions. The crystal structure of 1 indicates that the macrocycle adopts a cone shape in the solid state with all three ester groups on the same side and within the cone of the macrocycle. In contrast with the calixarenes, macrocycle 1 exhibits only a modest degree of cupping. 1H NMR spectra indicate that the cone and partial cone isomers of 1 are rapidly interconverting in the NMR timescale at room temperature. Macrocycle 1 exhibits no significant extraction of alkali metal picrates from aqueous solution.

Design, synthesis, and evaluation of mitomycin-tethered phosphorothioate oligodeoxynucleotides.

Mitomycin C (1) is the prototypical bioreductive alkylating agent. Studies have shown that mitomycin C and its derivatives selectively alkylate guanine residues within di- and trinucleotide DNA sequences. This investigation sought to improve the selective DNA bonding properties of the mitomycins by coupling them with antisense oligodeoxynucleotides. Two procedures were developed that allowed the attachment of a phosphorothioate oligodeoxynucleotide containing a hexylamino spacer at the 5' terminus with a C(10)-activated mitomycin. In the first procedure, decarbamoylation of 1 (NaOCH3/ benzene) afforded 10-decarbamoylmitomycin C (10), which was treated with either dimethyl sulfate or methylthiochloroformate and base to yield 10-decarbamoylporfiromycin (11) and N(1a)-[(methylthio)-carbonyl]-10-decarbamoylmitomycin C (12), respectively. Activation of the C(10) site in 11 and 12 with 1,1'-carbonyldiimidazole or with 1,1'-thiocarbonyldiimidazole provided the N(1a)-substituted mitomycin 10-decarbamoyl-10-O-carbonylimidazoles (5, 7) and 10-decarbamoyl-10-O-thiocarbonylimidazoles (6, 8), respectively. Compounds 5-8 were reacted with glycine methyl ester hydrochloride (17) and base in both methylene chloride and aqueous buffered solutions to determine the ease and efficiency in which these C(10)-activated mitomycin derivatives coupled to amines. It was found that 5-8 all reacted with 17 in methylene chloride to give the coupled products 18-21 but that improved amine coupling yields in water were observed for the 10-decarbamoyl-10-O-thiocarbonylimidazoles 6 and 8 as compared with the 10-decarbamoyl-10-O-carbonylimidazoles 5 and 7. This finding led to the coupling of the phosphorothioate oligodeoxynucleotide, H2N(CH2)6-P(S)(OH)-GGCCCCGTG-GTGGCTCCAT (22) to 8. Compound 22 complemented a 19-base sequence in the translation initiation region of the human A-raf-1 gene. Use of excess 8 (28 equiv) with 22 gave only a 36% yield of the coupled product 23, which proved difficult to separate from 22. In the second procedure, phosphorothioate oligodexynucleotides that contained a hexylamino spacer at the 5'termini were coupled to 10-des(carbamoyloxy)-10-isothiocyanatoporfiromycin (9). Compound 9 was prepared in four steps from 11. Mesylation (methanesulfonyl chloride/pyridine) of 11 gave the C(10) mesylate 13, which was then treated with NaN3 (dimethylformamide, 90 degrees C) to give 10-des(carbamoyloxy)-10-azidoporfiromycin (14). Catalytic reduction (PtO2, H2) of 14 in pyridine afforded C(10) amine 15. Treatment of 15 with di-2-pyridyl thionocarbonate provided the desired 10-des(carbamoyloxy)-10-isothiocyanatoporfiromycin (9). Compound 9 readily coupled with 17 and base in both methylene chloride and aqueous buffered solutions to give 25. Use of the 5'hexylaminophosphorothioate oligodeoxynucleotides 32-35 in place of 17 gave the conjugated adducts 28-31, respectively, in a 12% to near-quantitative yield. The products were purified by semipreparative HPLC. Antisense agents 28-31 were designed to target a 30-base-long region from the coding region of the human FGFR1 gene. One adduct, 29, reduced the number of FGFR1 receptors in human aortic smooth cells for bFGF on the cell surface, which suggested down-regulation of FGFR1 gene expression. Further, 29 inhibited cultured human aortic smooth muscle cell proliferation and was less cytotoxic than porfiromycin (2). The biological assay data suggest that the phosphorothioate oligodexynucleotide porfiromycin conjugates may be more target selective and less toxic than either mitomycin or porfiromycin and thus be promising therapeutic agents.

Preparation and reactions of epoxy-activated cellulose.

Cellulose acetate fibers were treated with sodium methoxide in methanol for replacing acetyl group with sodium atom. The resulting sodium-contaning cellulose was treated with epichlorohydrine (ECH) in DMSO for preparing epoxy-activated cellulose (CGE). The amount of epoxy group introduced into cellulose increasing with sodium-content but was independent of the reaction time, reaction temperature or ECH concentration. Besides epoxidation, some side reactions occured through ring-opening reaction of epoxy group. CGE could be converted to various functional cellulosic materials through reactions with substances containing active hydrogen, such as amines, amino acids or carboxylic acids. Polyethylenimine (PEI) reacted easily with CGE in DMF. The PEI content of the product and the conversion of epoxy groups increased with decrease in molecular weight of PEI. Other amines such as ammonia, methylamine, dimethylamine or 4-aminopyridine also reacted with CGE. Since methylamine and dimethylamine reacted with CGE in similar ways, the reactivity was considered to be similar with primary and secondary amino groups in PEI. Glycine also reacted with CGE in aqueous solution, and the degree of the reaction increased with increase in pH of the solution. Glycine methyl ester hydrochloride dissolved in DMSO reacted easily with CGE by adding basic compound such as 1, 8-diazabicyclo [5, 4, 0] undecene-7 (DBU). Some carboxylic acids including propionic, n-butyric and succinic acids also reacted readily with CGE, especially in the presence of DBU. However, the reactivity of succinic acid was lower than that of glycine in an aqueous alkaline solution, suggesting that the amino group of glycine was more reactive than the carboxyl group to CGE in aqueous solution.

Complexation between Saccharide and Ammonium Ion in Gas Phase. Regarding Stereochemical Effects of Methoxy Groups at Permethylated Monosaccharides on Stabilities of Cluster Ions in FAB Mass Spectrometry

Abstract The relative FABMS intensities of the cluster ions between permethylated monosaccharides and glycine methyl ester hydrochloride strongly suggest the configuration effect of the OCH3 groups, reflecting the relative stabilities of the cluster ions in gas phase.

Glycine methyl or ethyl ester hydrochloride as the simplest examples of salty peptides and their derivatives.

Glycine methyl or ethyl ester hydrochloride as the simplest examples of salty peptides and their derivatives.

Macroheterocycles. 12. Synthesis and properties of macrocyclic tetraamides

The N,N′-bis(methoxycarbonylmethyl)diamides of the corresponding acids were obtained by the reaction of glycine methyl ester hydrochloride with oxalic, succinic, adipic, diglycolic, and triglycolic acid dichlorides. Fourteen new macrocyclic tetraamides were obtained by the reaction of these diamides with various diamines. The structures of the synthesized compounds were proved by means of their IR, PMR, and mass spectra.