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Journal articles on the topic 'Carboxy esters'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Wagner, Michael, and Horst Kunz. "Der (2-Phenyl-2-trimethylsilyl)ethyl-(PTMSE)-Ester – eine neutral spaltbare Carboxyschutzgruppe/The (2-Phenyl-2-trimethylsiylyl)ethyl (PTMSE) Ester – a Carboxy Protecting Group Cleavable under Neutral Conditions." Zeitschrift für Naturforschung B 57, no. 8 (2002): 928–36. http://dx.doi.org/10.1515/znb-2002-0814.

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(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) esters of aminoacids and peptides are stable under the conditions of hydrogenolytic cleavage of benzoxycarbonyl(Z) and benzyl ester groups, base-induced removal of Fmoc groups, palladium(0)-catalyzed removal of allyloxycarbonyl (Aloc) and even acidolytic cleavage of Boc groups. PTMSE esters are also stable under the conditions of peptide condensation reactions. The PTMSE ester is selectively cleaved by treatment with tetrabutylammonium fluoride (TBAF) trihydrate in dichloromethane, i. e. under almost neutral conditions, within a few minutes and, therefo

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2

Tamiaki, Hitoshi, Kouji Kumon, and Reiko Shibata. "Synthetic hydroxymethyl-porphyrins for protection of carboxy group." Journal of Porphyrins and Phthalocyanines 11, no. 06 (2007): 434–41. http://dx.doi.org/10.1142/s1088424607000497.

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Hydroxymethyl-porphyrins were prepared by modifying tetraarylporphyrin possessing a p-(methoxycarbonyl)phenyl group at the meso-position and octaethylporphyrin. The synthetic alcohols reacted with carboxylic acids by the use of coupling reagents, to give the corresponding esters quantitatively. Due to the porphyrin dye moiety, the esterification was easily monitored on thin layer chromatography, and the resulting esters were highly soluble in most organic solvents and easily handled. The esters were readily cleaved by the action of an acid to give the original carboxylic acid and hydroxymethyl

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3

Neogi, Partha, Sujata Neogi, and Charles J. M. Stirling. "Reactivity of carboxy esters in gold–thiol monolayers." J. Chem. Soc., Chem. Commun., no. 14 (1993): 1134–36. http://dx.doi.org/10.1039/c39930001134.

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4

Cole, S. C. J., and R. J. Yon. "Carrot cells detoxify N-phosphonoacetyl-l-aspartate by esterification." Biochemical Journal 255, no. 3 (1988): 813–16. http://dx.doi.org/10.1042/bj2550813.

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Unlike bacterial and mammalian cells, carrot cells are able to tolerate N-phosphonoacetyl-L-aspartate (PALA), a potential inhibitor of pyrimidine biosynthesis, by detoxifying the compound. Anion-exchange chromatography showed that detoxified PALA was less negatively charged than PALA, and allowed detoxified PALA to be isolated. Incubation of detoxified PALA with a low-specificity carboxylic-ester hydrolase fully restored the ability to inhibit aspartate transcarbamoylase, the target enzyme, indicating that the detoxification involves the formation of carboxylic ester. G.1.c. analysis of the al

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5

Parsons, Harriet T., Tayyaba Yasmin, and Stephen C. Fry. "Alternative pathways of dehydroascorbic acid degradation in vitro and in plant cell cultures: novel insights into vitamin C catabolism." Biochemical Journal 440, no. 3 (2011): 375–85. http://dx.doi.org/10.1042/bj20110939.

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L-Ascorbate catabolism involves reversible oxidation to DHA (dehydroascorbic acid), then irreversible oxidation or hydrolysis. The precursor–product relationships and the identity of several major DHA breakdown products remained unclear. In the presence of added H2O2, DHA underwent little hydrolysis to DKG (2,3-dioxo-L-gulonate). Instead, it yielded OxT (oxalyl L-threonate), cOxT (cyclic oxalyl L-threonate) and free oxalate (~6:1:1), essentially simultaneously, suggesting that all three product classes independently arose from one reactive intermediate, proposed to be cyclic-2,3-O-oxalyl-L-thr

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6

Valenta, Vladimír, Jiří Holubek, Emil Svátek, and Miroslav Protiva. "Potential cholinergic and anticholinergic compounds: Synthesis of 2,8-substituted 2,8-diazaspiro[4,5]decane-1,3-diones." Collection of Czechoslovak Chemical Communications 55, no. 9 (1990): 2304–16. http://dx.doi.org/10.1135/cccc19902304.

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Heating the ammonium salt of (4-carboxy-1-methyl-4-piperidinyl)acetic acid (XII) gave 8-methyl-2,8-diazaspiro[4,5]decane-1,3-dione (II) which was N-alkylated with 2-bromoethanol and 4-bromobutanol to give the alcohols III and V. Compound III was transformed to the chloro compound VI which was reacted with the sodium salt of hexahydrobenzilic acid to give the ester VII. Compound V was transformed to the 4-toluenesulfonic ester VIII which reacted with 1-(2-pyrimidinyl)piperazine and gave IX. 2-(2-Propyl)-2,8-diazaspiro[4,5]decane-1,3-dione (XVIII) was similarly transformed via XIX to XX which re

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7

Mirčeva, Aneta, Majda Žigon, Mira Mikuž, Tatjana Malavašič, and Uči Osredkar. "Study of the epoxy–carboxy reaction: Curing of brominated epoxy esters containing free carboxyl groups." Journal of Applied Polymer Science 48 (1991): 481–92. http://dx.doi.org/10.1002/app.1991.070480036.

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8

Klabenkova, Kristina V., Polina V. Zhdanova, Ekaterina A. Burakova, Sergei N. Bizyaev, Alesya A. Fokina, and Dmitry A. Stetsenko. "A Convenient Oligonucleotide Conjugation via Tandem Staudinger Reaction and Amide Bond Formation at the Internucleotidic Phosphate Position." International Journal of Molecular Sciences 25, no. 4 (2024): 2007. http://dx.doi.org/10.3390/ijms25042007.

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Staudinger reaction on the solid phase between an electronodeficit organic azide, such as sulfonyl azide, and the phosphite triester formed upon phosphoramidite coupling is a convenient method for the chemical modification of oligonucleotides at the internucleotidic phosphate position. In this work, 4-carboxybenzenesulfonyl azide, either with a free carboxy group or in the form of an activated ester such as pentafluorophenyl, 4-nitrophenyl, or pentafluorobenzyl, was used to introduce a carboxylic acid function to the terminal or internal internucleotidic phosphate of an oligonucleotide via the

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9

Bunce, Richard A., та Demck M. Herrod. "A SYNTHESIS OF (E)-ω-CARBOXY-2-ALKENOIC ESTERS". Organic Preparations and Procedures International 32, № 6 (2000): 577–80. http://dx.doi.org/10.1080/00304940009355955.

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10

Tolman, Vladimír, and Petr Sedmera. "Some New Derivatives of 2-Pentenedioic Acid." Collection of Czechoslovak Chemical Communications 58, no. 6 (1993): 1430–36. http://dx.doi.org/10.1135/cccc19931430.

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Michael addition of N-acylaminomalonates to propynoic esters led to the (E)-4-acylamino)-4-carboxy-2-pentenedioic triesters IIa - IIf. On deprotection and decarboxylation, these compounds afforded 2-(N-acylamino)-2-pentenedioic acid derivatives IIIa - IIIc. Dimethyl (E)-4-diazo-2-pentenedioate (IV) was prepared by direct transfer of the diazo group. On treatment of IV with 4-toluenesulfonic acid, 2-(4-toluenesulfonyloxy)-2-pentenedioate (V) was formed. Iodination of (E)-2-pentenedioic acid led directly to the 2,4-diododerivative VII. From dimethyl (E)-4-oxo-2-pentenedioate the oximino ester VI

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11

Ionita, Petre, Floriana Tuna, Marius Andruh, Titus Constantinescu, and Alexandru T. Balaban. "Synthesis and Characterization of Some Novel Homo- and Hetero-Diradicals of Hydrazyl and Nitroxide Type." Australian Journal of Chemistry 60, no. 3 (2007): 173. http://dx.doi.org/10.1071/ch06469.

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Starting from the well known stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH; 2a) and its congener 2,2-diphenyl-1-(4-cyano-2,6-dinitrophenyl)hydrazyl 2b, or from their reduced hydrazine counterparts 1a,b, it was possible to obtain the p-quinonoid compounds 4a,b by oxidation with ceric (Ce4+) sulfate, which by reduction gave the corresponding hydroxyl derivatives 2-phenyl-2-(4-hydroxyphenyl)-1-picrylhydrazine 5a or 2-phenyl-2-(4-hydroxyphenyl)-1-(4-cyano-2,6-dinitrophenyl)hydrazine 5b. These hydroxyl derivatives (5a,b) react with 4-carboxy-TEMPO or 2,2-diphenyl-1-(4-carboxy-2,6-dinitrop

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12

Palos, Isidro, Rosa Moo-Puc, José Luis Vique-Sánchez, et al. "Esters of quinoxaline-7-carboxylate-1,4-di-N-oxide as Trichomonas vaginalis triosephosphate isomerase inhibitors." Acta Pharmaceutica 71, no. 3 (2020): 485–95. http://dx.doi.org/10.2478/acph-2021-0032.

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Abstract Trichomoniasis is a public health problem worldwide. Trichomoniasis treatment consists of the use of nitroimidazole derivatives; however, therapeutic ineffectiveness occurs in 5 to 20 % of the cases. Therefore, it is essential to propose new pharmacological agents against this disease. In this work, esters of quinoxaline-7-carboxylate-1,4-di-N-oxide (EQX-NO) were evaluated in in vitro assays as novel trichomonicidal agents. Additionally, an in vitro enzyme assay and molecular docking analysis against triosephosphate isomerase of Trichomonas vaginalis to confirm their mechanism of acti

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13

Boykin, David W., and Arvind Kumar. "17O NMR spectroscopy: Intramolecular hydrogen bonding in hydroxypyridine carboxy esters." Journal of Heterocyclic Chemistry 29, no. 1 (1992): 1–4. http://dx.doi.org/10.1002/jhet.5570290101.

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14

Baskal, Svetlana, Alexander Bollenbach, and Dimitrios Tsikas. "GC-MS Discrimination of Citrulline from Ornithine and Homocitrulline from Lysine by Chemical Derivatization: Evidence of Formation of N5-Carboxy-ornithine and N6-Carboxy-lysine." Molecules 26, no. 8 (2021): 2301. http://dx.doi.org/10.3390/molecules26082301.

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Derivatization of amino acids by 2 M HCl/CH3OH (60 min, 80 °C) followed by derivatization of the intermediate methyl esters with pentafluoropropionic anhydride (PFPA) in ethyl acetate (30 min, 65 °C) is a useful two-step derivatization procedure (procedure A) for their quantitative measurement in biological samples by gas chromatography-mass spectrometry (GC-MS) as methyl ester pentafluoropropionic (PFP) derivatives, (Me)m-(PFP)n. This procedure allows in situ preparation of trideutero-methyl esters PFP derivatives, (d3Me)m-(PFP)n, from synthetic amino acids and 2 M HCl/CD3OD for use as intern

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15

Marton, János, Brita Glaenzel, Julia Roessler, Daniela Golaszewski, and Gjermund Henriksen. "A Convenient Route to 4-Carboxy-4-Anilidopiperidine Esters and Acids." Molecules 17, no. 3 (2012): 2823–32. http://dx.doi.org/10.3390/molecules17032823.

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16

Bunce, Richard A., та Derrick M. Herron. "ChemInform Abstract: A Synthesis of (E)-ω-Carboxy-2-alkenoic Esters." ChemInform 32, № 17 (2001): no. http://dx.doi.org/10.1002/chin.200117063.

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17

V, S. JOLLY, Y. DALVI M., and K. SHRIVASTAVA A. "Studies on Pyrazolones. Part-III. Synthesis, Dyeing and Antifungal Activity of some 1-Substituted-3-phenyl-4-(2/4-carboxyphenylazo)-5-pyrazolones." Journal of Indian Chemical Society Vol. 68, Sep 1991 (1991): 513–14. https://doi.org/10.5281/zenodo.5970727.

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Chemical Laboratories, Government Model Science College, Gwalior·474 002 <em>Manuscript received 18 February 1991, revised 29 May 1991, accepted 3 September 1991</em> A series of new pyrazolones and esters have been synthesised. Treatment of ethyl benzoylacetate with diazotistd 2/4-aminobenzoic acid gave ethyl 2-(2/4-carboxy-phenylazo)-2-benzoylacetates. Reaction of the esters with anilinomalonic acid hydrazides gave 1-sutstituted-2-phenyl-4-(2/4-carboxyphenylazo)-5-pyrazolones. The dyes impart mostly light yellow colour of different shades on cotton, silk and wool fibres and light oran

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18

Svensson, B. E. "Thiols as myeloperoxidase-oxidase substrates." Biochemical Journal 253, no. 2 (1988): 441–49. http://dx.doi.org/10.1042/bj2530441.

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Nine low-Mr thiols were compared with regard to their ability to function as myeloperoxidase-oxidase substrates under conditions where no auto-oxidation of the thiols could be observed. The methyl and ethyl esters of cysteine were found to be about twice as active as cysteamine at pH 7.0, in terms of increased O2 consumption. Cysteine itself was poorly active, whereas glutathione, N-acetylcysteine and penicillamine were completely inactive as myeloperoxidase-oxidase substrates under these conditions. The structure-activity relationships indicated that both a free thiol and free amino group wer

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19

Ricardo, Tovar Mir, a, Corteacute s. Garciacute a. Rauacute l, et al. "Enzymatic hydrolysis of esters from 2-carboxy-6-methoxy-2,3-dihydrobenzofuran acid." African Journal of Biotechnology 8, no. 21 (2009): 5958–63. http://dx.doi.org/10.5897/ajb09.1092.

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20

Friedrich-Bochnitschek, Sieglinde, Herbert Waldmann, and Horst Kunz. "Allyl esters as carboxy protecting groups in the synthesis of O-glycopeptides." Journal of Organic Chemistry 54, no. 4 (1989): 751–56. http://dx.doi.org/10.1021/jo00265a007.

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21

BOYKIN, D. W., and A. KUMAR. "ChemInform Abstract: 17O NMR Spectroscopy: Intramolecular Hydrogen Bonding in Hydroxypyridine Carboxy Esters." ChemInform 23, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199230027.

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22

Calonghi, Natalia, Carla Boga, Dario Telese, et al. "Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells." Molecules 24, no. 20 (2019): 3714. http://dx.doi.org/10.3390/molecules24203714.

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9-Hydroxystearic acid (9-HSA) is an endogenous cellular lipid that possesses antiproliferative and selective effects against cancer cells. A series of derivatives were synthesized in order to investigate the effect of the substituent in position 9 and on the methyl ester functionality on the biological activity. The two separate enantiomers of methyl 9-hydroxystearate and of methyl 9-aminostearate showed antiproliferative activity against the HT29 cell line. This indicates the importance of position 9 groups being able to make hydrogen bonding with the molecular target. Further, this effect mu

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23

Belostotskaya, I. S., V. B. Vol’eva, N. C. Domnina, et al. "Synthesis and properties of macromolecular esters of carboxy-substituted derivatives of hindered phenols." Russian Journal of Organic Chemistry 46, no. 11 (2010): 1652–57. http://dx.doi.org/10.1134/s1070428010110060.

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24

Wang, Yong, та Reji Nair. "Synthesis of 4-carboxy-4-pyridylpiperidines through palladium-catalyzed α-arylation of esters". Tetrahedron Letters 48, № 7 (2007): 1191–93. http://dx.doi.org/10.1016/j.tetlet.2006.12.052.

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25

Nagano, Yasunobu, Shin Ogasawara, and Hitoshi Tamiaki. "Regioisomeric synthesis of chlorin-e6 dimethyl esters and their optical properties." Journal of Porphyrins and Phthalocyanines 22, no. 12 (2018): 1039–46. http://dx.doi.org/10.1142/s1088424618501043.

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Chlorin-[Formula: see text] dimethyl esters possessing a single carboxy group at the 13-, 151-, or 172-position were prepared by chemically modifying chlorophyll-[Formula: see text]. These three synthetic regioisomers were fully characterized by their mass, NMR, and visible absorption spectra. Their molecular structures were unambiguously identified by the specific 1H–[Formula: see text]C correlation at the 13-, 15-, and/or 17-substituents in their respective HMBC spectra. Methyl esterification of 13/151-COOH and hydrolysis of 13/151-COOMe affected small shifts of the Qy absorption and fluores

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26

Lawrance, GA, BW Skelton, AH White, and EN Wilkes. "Tetraazacycloalkanes With Pendant Carboxylates. Copper(II)-Directed Syntheses and Crystal Structure of (Ethyl 1,5,9,13-tetraazabicyclo[11.2.2]heptadecane-7-carboxylate)copper(II) Perchlorate." Australian Journal of Chemistry 44, no. 11 (1991): 1511. http://dx.doi.org/10.1071/ch9911511.

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Reaction of copper(II) complexes of the tetraamines H2N-(CH2)n-NH-(CH2)m-NH-(CH2)n-NH2 (n, m=5, 6), N,N′- bis (3-aminopropyl)-1,4-diazacyclohexane and ethane-1,2-diamine with formaldehyde and diethyl malonate in methanolic base produces macrocycles where initially new -NH-CH2-C( COOEt )2-CH2-NH-links are built by joining the cis-disposed primary amines in the precursor complexes. Under the basic conditions of the reaction, the macrocyclic product may be isolated not simply with gem ethoxycarbonyl groups, but as the carboxy ethoxycarbonyl, or even with a single carboxy pendant or its ester foll

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27

Čeřovský, Václav, Jana Pírková, Pavel Majer, Jiřina Slaninová, and Jan Hlaváček. "Papain-catalyzed fragment synthesis of protected cholecystokinin derivatives." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1873–82. http://dx.doi.org/10.1135/cccc19901873.

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Sodium salts of methyl esters of N-tert-butyloxycarbonyl-β-tert-butylaspartyl-O4-sulfotyrosine (II) or N-tert-butyloxycarbonyl-O4-sulfotyrosine (III) were condensed with amino components derived from peptide amides IVb-IVe and IVg (simulating the carboxy-terminal part of cholecystokinin) under catalysis with papain. Rates and yields of conversion of these peptides to the corresponding derivatives Ib-If were compared with the results reported previously for analogous papain-catalyzed fragment synthesis of the protected carboxy-terminal octapeptide of cholecystokinin Ia. In the condensation reac

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28

Scaffidi, Adrian, Brian W. Skelton, Robert V. Stick та Allan H. White. "The Synthesis of Carbohydrate α-Amino Acids Utilizing the Corey - Link Reaction". Australian Journal of Chemistry 57, № 8 (2004): 723. http://dx.doi.org/10.1071/ch04015.

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Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey–Link reaction (sodium azide and 1,8-diazabicyclo[5.4.0]undec-7-ene in methanol), generally gave the expected azido ester with complete stereocontrol. Subsequent transformations on these azido esters provided amino esters, azido acids, and, in one case, the amino acid. A similar sequence applied to a protected d-glucono-1,5-lactone was only partly successful. Single-crystal X-ray

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29

Romzek, Nadine C., Estelle S. Harris, Cheryl L. Dell та ін. "Use of a β1 Integrin-deficient Human T Cell to Identify β1 Integrin Cytoplasmic Domain Sequences Critical for Integrin Function". Molecular Biology of the Cell 9, № 10 (1998): 2715–27. http://dx.doi.org/10.1091/mbc.9.10.2715.

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T cell activation rapidly and transiently regulates the functional activity of integrin receptors. Stimulation of CD3/T cell receptor, CD2 or CD28, as well as activation with phorbol esters, can induce within minutes an increase in β1 integrin-mediated adhesion of T cells to fibronectin. In this study, we have produced and utilized a mutant of the Jurkat T cell line, designated A1, that lacks protein and mRNA expression of the β1 integrin subunit but retains normal levels of CD2, CD3, and CD28 on the cell surface. Activation-dependent adhesion of A1 cells to fibronectin could be restored upon

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30

van Nuland, Youri M., Gerrit Eggink та Ruud A. Weusthuis. "Application of AlkBGT and AlkL from Pseudomonas putida GPo1 for Selective Alkyl Ester ω-Oxyfunctionalization in Escherichia coli". Applied and Environmental Microbiology 82, № 13 (2016): 3801–7. http://dx.doi.org/10.1128/aem.00822-16.

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ABSTRACTThe enzyme system AlkBGT fromPseudomonas putidaGPo1 can efficiently ω-functionalize fatty acid methyl esters. Outer membrane protein AlkL boosts this ω-functionalization. In this report, it is shown that whole cells ofEscherichia coliexpressing the AlkBGT system can also ω-oxidize ethyl nonanoate (NAEE). Coexpression of AlkBGT and AlkL resulted in 1.7-fold-higher ω-oxidation activity on NAEE. With this strain, initial activity on NAEE was 70 U/g (dry weight) of cells (gcdw), 67% of the initial activity on methyl nonanoate. In time-lapse conversions with 5 mM NAEE the main product was 9

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31

Slayman, C. L., V. V. Moussatos, and W. W. Webb. "Endosomal accumulation of pH indicator dyes delivered as acetoxymethyl esters." Journal of Experimental Biology 196, no. 1 (1994): 419–38. http://dx.doi.org/10.1242/jeb.196.1.419.

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Intracellular distributions of the putative cytosolic pH indicator dyes BCECF [2',7'-bis-(2-carboxyethyl)-5(and 6)-carboxyfluorescein], C.SNARF [5(and 6)-carboxy-seminaphthorhodafluor-1], and C.SNARF-calcein have been examined in Neurospora crassa and in murine fibroblasts (NIH-3T3 cells) under conditions in which both kinds of cells produce visible microscopic vacuoles. All three dyes were administered in electroneutral forms, with the hydroxyl and carboxyl groups esterified (designated as -AM esters). As judged qualitatively from fluorescence levels, hydrolytic derivatives of the two heavily

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32

Wood, Paul L. "Fatty Acyl Esters of Hydroxy Fatty Acid (FAHFA) Lipid Families." Metabolites 10, no. 12 (2020): 512. http://dx.doi.org/10.3390/metabo10120512.

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Fatty Acyl esters of Hydroxy Fatty Acids (FAHFA) encompass three different lipid families which have incorrectly been classified as wax esters. These families include (i) Branched-chain FAHFAs, involved in the regulation of glucose metabolism and inflammation, with acylation of an internal branched-chain hydroxy-palmitic or -stearic acid; (ii) ω-FAHFAs, which function as biosurfactants in a number of biofluids, are formed via acylation of the ω-hydroxyl group of very-long-chain fatty acids (these lipids have also been designated as o-acyl hydroxy fatty acids; OAHFA); and (iii) Ornithine-FAHFAs

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33

Easton, CJ, S. Kassara, SF Lincoln, and BL May. "Amino Substituents as a Probe of Reactions of Phenyl Acetates With Cyclodextrins." Australian Journal of Chemistry 48, no. 2 (1995): 269. http://dx.doi.org/10.1071/ch9950269.

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The effects of α- and β- cyclodextrin and 6A-amino-6A-deoxy-α- and -β- cyclodextrin on the rates of reactions of m- and p-nitrophenyl acetate, in borate buffer at pH 10.0 and 298.2 K, show that the amino substituents of the modified cyclodextrins have only a modest influence on the dissociation constants of the complexes formed with each ester and the first-order rate constants for the reactions of complexed m-nitrophenyl acetate. By contrast, the amino substituents significantly increase the rate constants for the reactions of complexes of p- nitrophenyl acetate. These results indicate that o

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34

Torlopov, M. A., E. V. Buravlev, O. V. Sukrusheva, and I. Yu Chukicheva. "Synthesis of esters of 2,6-diisobornyl-4-methylphenol carboxy-containing derivatives with hydroxyethyl starch." Russian Chemical Bulletin 63, no. 9 (2014): 2201–4. http://dx.doi.org/10.1007/s11172-014-0721-5.

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35

Guthrie, O'neil W., Caroline A. Gearhart, Sherry Fulton, and Laurence D. Fechter. "Carboxy alkyl esters of Uncaria tomentosa augment recovery of sensorineural functions following noise injury." Brain Research 1407 (August 2011): 97–106. http://dx.doi.org/10.1016/j.brainres.2011.06.044.

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36

Palomo, Claudio, Jesús M. Aizpurua, Iñaki Ganboa та Mikel Oiarbide. "Versatility of β-lactams in synthesis. Studies directed toward the synthesis of complex nucleoside antibiotics and some macrocyclic peptides". Pure and Applied Chemistry 72, № 9 (2000): 1763–68. http://dx.doi.org/10.1351/pac200072091763.

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The diastereoselective [2+2] cycloaddition of α-hydroxyketene equivalents with chiral α,ω-oxyaldehyde-derived imines followed by the 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO)-promoted ring expansion of the resulting α-hydroxy β-lactam adducts provides an unconventional and short route to α-amino acid N-carboxy anhydrides (NCAs). The required enantiopure α,ω-oxyaldehydes were obtained either from the chiral pool or through the Sharpless AD methodology. Following the present strategy, several nonproteinogenic NCAs were synthesized, which were further coupled with α-amino acid esters giving r

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37

Ledvina, Miroslav, and Jiří Farkaš. "Cyclization Dichotomy of Esters of 3-Ureido-2-cyano-2-propenoic and 3-Ureido-2-acyl-2-propenoic Acids." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1841–52. http://dx.doi.org/10.1135/cccc19941841.

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The preparation of E and Z isomers of 3-ureido-2-cyano-2-propenoates Ia - Id and their base-catalyzed isomerization and cyclization to 5-carboxycytosine derivatives IIa - IIf and 5-cyanouracil derivatives IIIa and IIIb is described. Also described is the preparation of 3-ureido-2-acyl-2-propenoates Va - Vd and their base-catalyzed cyclization to 5-carboxy-2(1H)-pyrimidone derivatives VIa - VIc and 5-acyluracils VIIa - VIIc.

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38

Braun, Peter, Herbert Waldmann, Walter Vogt, and Horst Kunz. "Selective Enzymatic Removal of Protecting Functions: Heptyl Esters as Carboxy Protecting Groups in Peptide Synthesis." Synlett 1990, no. 02 (1990): 105–7. http://dx.doi.org/10.1055/s-1990-21002.

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39

Braun, Peter, Herbert Waldmann, and Horst Kunz. "Selective Enzymatic Removal of Protecting Functions: Heptyl Esters as Carboxy Protecting Groups in Glycopeptide Synthesis." Synlett 1992, no. 01 (1992): 39–40. http://dx.doi.org/10.1055/s-1992-21258.

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40

Kashparova, V. P., E. N. Shubina, D. V. Tokarev, G. P. Antropov, and I, Yu Zhukova. "UNIVERSAL ELECTROCATALYTIC SYSTEM FOR CONVERSION OF ALCOHOLS INTO CARBONYL COMPOUNDS AND CARBOXY ACID FUNCTIONAL DERIVATIVES." Электрохимия 59, no. 10 (2023): 579–92. http://dx.doi.org/10.31857/s0424857023100079.

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A universal catalytic system 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl/KI/pyridine base for the conversion of alcohols into carbonyl compounds and derivatives of carboxylic acids has been developed. The use of pyridine, 2,6-lutidine or collidine made it possible to obtain carbonyl compounds (yield up to 100%) after 2-2.2 F/mol. In the presence of pyridine, aliphatic alcohols are converted to esters (yield up to 35%) after 3-4 F/mol. Acid anhydrides (yield up to 80%) are formed using 2,6-lutidine or collidine after 5-6 F/mol. Nitriles were obtained in the presence of 2,6-lutidine and a s

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41

Čebular, Klara, Bojan Božić, and Stojan Stavber. "Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions." Molecules 23, no. 9 (2018): 2235. http://dx.doi.org/10.3390/molecules23092235.

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N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedu

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42

Asahara, Haruyasu, Keita Arikiyo, and Nagatoshi Nishiwaki. "Development of variously functionalized nitrile oxides." Beilstein Journal of Organic Chemistry 11 (July 23, 2015): 1241–45. http://dx.doi.org/10.3762/bjoc.11.138.

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N-Methylated amides (N,4-dimethylbenzamide and N-methylcyclohexanecarboxamide) were systematically subjected to chemical transformations, namely, N-tosylation followed by nucleophilic substitution. The amide function was converted to the corresponding carboxylic acid, esters, amides, aldehyde, and ketone upon treatment with hydroxide, alkoxide, amine, diisobutylaluminium hydride and Grignard reagent, respectively. In these transformations, N-methyl-N-tosylcarboxamides behave like a Weinreb amide. Similarly, N-methyl-5-phenylisoxazole-3-carboxamide was converted into 3-functionalized isoxazole

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43

Riabchenko, Anastasiia, Olga Shablykina, Serhiy Shilin, Svitlana Chumachenko, and Volodymyr Khilya. "Amino acid sulfonamides based on 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride." Ukr. Bioorg. Acta 2020, Vol. 15, N2 15, no. 2 (2020): 27–32. http://dx.doi.org/10.15407/bioorganica2020.02.027.

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The creation of new amino acid derivatives of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride 1 was investigated. The interaction of the sulfonyl chloride 1 with amino acid methyl esters (hydrochlorides) in 1,4-dioxane in the presence of triethylamine led to the corresponding amino acid sulfonamide derivatives of isocoumarin. The reaction of the sulfonyl chloride 1 with phenylalanine in the basic aqueous solution was complicated by the lactone system disclosure and led to 2'-carboxydeoxybenzoin ultimately (namely, 2-(2-(4-(N-(1-carboxy-2-phenylethyl)sulfamoyl)phenyl)-2-oxoethyl)benzoic ac

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44

Meldal, Morten, та Knud J. Jensen. "Pentafluorophenyl esters for the temporary protection of the α-carboxy group in solid phase glycopeptide synthesis". J. Chem. Soc., Chem. Commun., № 6 (1990): 483–85. http://dx.doi.org/10.1039/c39900000483.

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45

Heiman, Ann S., Irach B. Taraporewala, Hugh M. McLean, Deasik Hong, and Henry J. Lee. "New potent topical anti-inflammatory steroids with reduced side effects: Derivatives of steroid-16-carboxy esters." Journal of Pharmaceutical Sciences 79, no. 7 (1990): 617–21. http://dx.doi.org/10.1002/jps.2600790716.

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46

A. Al-Dawaf, Rana, and Kawkab Y. Saour. "Synthesis of Coumarin Derivatives Coupled to Amino Acid Esters and Studying their Biological Activity as Antimicrobial Agents." Iraqi Journal of Pharmaceutical Sciences ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 21, no. 2 (2017): 1–7. http://dx.doi.org/10.31351/vol21iss2pp1-7.

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A series of coumarin derivatives linked to amino acid ester side chains were synthesized and evaluated of their antibacterial and antifungal activity. The coumarin derivatives was alkylated by the ethyl bromoacetate and then using potassium carbonate to get alkylated hymecromone. Conventional solution method for amide bond formation was used as a coupling method between the carboxy-protected amino acids with acetic acid side chain of coumarin derivatives. The DCC/ HOBt coupling reagents were used for peptide bond formation. The proposed analogues were successfully synthesized and their structu

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47

Brandl, Helmut, Brigitte Aeberli, Reinhard Bachofen, et al. "Biodegradation of cyclic and substituted linear oligomers of poly(3-hydroxybutyrate)." Canadian Journal of Microbiology 41, no. 13 (1995): 180–86. http://dx.doi.org/10.1139/m95-185.

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Cyclic oligo(3-hydroxybutyrate), oligo(3-HB), was synthesized and purified, resulting in oligolides that contained three to seven (R)-3-hydroxybutyrate units (triolides up to heptolides). In addition, linear 3-HB octamers obtained as either tert-butyl or methyl esters were substituted with different end groups at the hydroxy end. The hydroxy terminus was replaced by either a benzyloxy, trifluoroacetoxy, crotonyloxy, (S)-3-hydroxybutyryloxy, or fluorenylmethylcarbonyloxy (FMOC) group. P(3-HB) hairpin loops occurred on the surface of certain regions of the polymer, especially of lamellar crystal

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48

Waldmann, Herbert, and Horst Kunz. "1,3-Dithian-2-ylmethyl esters as two-step carboxy-protecting groups in the synthesis of N-glycopeptides." Journal of Organic Chemistry 53, no. 18 (1988): 4172–75. http://dx.doi.org/10.1021/jo00253a003.

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49

Effenberger, Franz, Wolfgang Mueller, Roland Keller, Wolfgang Wild, and Thomas Ziegler. "Amino acids. 8. A novel synthesis of .gamma.-carboxy-L-glutamic acid from L-5-oxoproline esters." Journal of Organic Chemistry 55, no. 10 (1990): 3064–67. http://dx.doi.org/10.1021/jo00297a022.

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50

Collard, Jean-François, and Yves Raymond. "Phorbol esters induce transient changes in the accessibility of the carboxy-terminal domain of nuclear lamin A." Experimental Cell Research 201, no. 1 (1992): 174–83. http://dx.doi.org/10.1016/0014-4827(92)90361-b.

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