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Journal articles on the topic 'Quaternary amino acids'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Jørgensen, K., S. Cabrera, E. Reyes, J. Alemán, A. Milelli та S. Kobbelgaard. "Quaternary α-Amino Acids and Derivatives". Synfacts 2008, № 11 (2008): 1220. http://dx.doi.org/10.1055/s-0028-1083383.

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2

Haugen, J. E., H. P. Sejrup, and N. B. Vogt. "Chemotaxonomy of Quaternary benthic foraminifera using amino acids." Journal of Foraminiferal Research 19, no. 1 (1989): 38–51. http://dx.doi.org/10.2113/gsjfr.19.1.38.

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3

Szponar, A., and L. Szajdak. "Amino acids in Quaternary soil horizons from southwest Poland." European Journal of Soil Science 54, no. 2 (2003): 237–42. http://dx.doi.org/10.1046/j.1365-2389.2003.00536.x.

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4

Hano, Tadashi, Takaaki Ohtake, Michiaki Matsumoto, Daihachi Kitayama, Fumiaki Hori, and Fumiyuki Nakashio. "Extraction equilibria of amino acids with quaternary ammonium salt." JOURNAL OF CHEMICAL ENGINEERING OF JAPAN 24, no. 1 (1991): 20–24. http://dx.doi.org/10.1252/jcej.24.20.

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5

Jiang, Shende, Guang Yang, Shuanglin Qin та ін. "An Efficient Method for Constructing Cyclic β-Amino Acids Bearing Quaternary Stereocenters". Synlett 30, № 05 (2019): 593–99. http://dx.doi.org/10.1055/s-0037-1611718.

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This paper describes an efficient method for constructing cyclic β-amino acids bearing quaternary stereocenters. NaHMDS-promoted asymmetric α-alkylation was employed to obtain the key intermediates with quaternary stereogenic centers, which were subsequently reduced by NaBH4 in 10% methanol in THF, with high yields and high diastereoselectivities. By removing the allyl ester group and the chiral auxiliary, the corresponding cyclic β-amino acid hydrochlorides were finally obtained.

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6

Picard, Audrey, Stephane Ciblat та Yeeman K. Ramtohul. "Synthesis of α,α-Disubstituted Benzocyclobutane Amino Acids through [2+2] Annulation of Benzyne with Dehydroalanine". Synlett 31, № 05 (2020): 507–11. http://dx.doi.org/10.1055/s-0039-1691572.

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A mild and general method for the synthesis of α,α-disubstituted benzocyclobutane amino acids through a [2+2] annulation of benzyne with dehydroalanine is described. Yields up to 88% of the constrained quaternary amino acids can be obtained and its application in peptidomimetic synthesis is demonstrated.

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7

Davies, Stephen G., A. Christopher Garner, Jaqueline V. A. Ouzman та ін. "Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates". Org. Biomol. Chem. 5, № 13 (2007): 2138–47. http://dx.doi.org/10.1039/b704475e.

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8

Gómez, José Enrique, Wusheng Guo, Silvia Gaspa та Arjan W. Kleij. "Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters". Angewandte Chemie International Edition 56, № 47 (2017): 15035–38. http://dx.doi.org/10.1002/anie.201709511.

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9

Mata, Lara, Alberto Avenoza, Jesús H. Busto, Francisco Corzana та Jesús M. Peregrina. "Quaternary Chiral β2,2-Amino Acids with Pyridinium and Imidazolium Substituents". Chemistry - A European Journal 18, № 49 (2012): 15822–30. http://dx.doi.org/10.1002/chem.201202096.

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10

Gómez, José Enrique, Wusheng Guo, Silvia Gaspa та Arjan W. Kleij. "Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters". Angewandte Chemie 129, № 47 (2017): 15231–34. http://dx.doi.org/10.1002/ange.201709511.

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11

Larionov, Vladimir A., Nadezhda V. Stoletova, Vladislav I. Kovalev, Alexander F. Smol'yakov, Tat'yana F. Savel'yeva та Victor I. Maleev. "A general synthesis of unnatural α-amino acids by iron-catalysed olefin–olefin coupling via generated radicals". Organic Chemistry Frontiers 6, № 8 (2019): 1094–99. http://dx.doi.org/10.1039/c9qo00108e.

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12

Kimura, Yuto, Daisuke Uraguchi та Takashi Ooi. "Catalytic asymmetric synthesis of 5-membered alicyclic α-quaternary β-amino acids via [3 + 2]-photocycloaddition of α-substituted acrylates". Organic & Biomolecular Chemistry 19, № 8 (2021): 1744–47. http://dx.doi.org/10.1039/d1ob00126d.

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13

Cativiela, Carlos, та Marı́a Dolores Dı́az-de-Villegas. "Stereoselective synthesis of quaternary α-amino acids. Part 2: Cyclic compounds". Tetrahedron: Asymmetry 11, № 3 (2000): 645–732. http://dx.doi.org/10.1016/s0957-4166(99)00565-0.

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14

Cativiela, Carlos, та Marı́a Dolores Dı́az-de-Villegas. "Stereoselective synthesis of quaternary α-amino acids. Part 1: Acyclic compounds". Tetrahedron: Asymmetry 9, № 20 (1998): 3517–99. http://dx.doi.org/10.1016/s0957-4166(98)00391-7.

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15

Shymanska, Nataliia V., та Joshua G. Pierce. "Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids". Organic Letters 19, № 11 (2017): 2961–64. http://dx.doi.org/10.1021/acs.orglett.7b01185.

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16

Husmann, Ralph, Erli Sugiono, Stefanie Mersmann, Gerhard Raabe, Magnus Rueping та Carsten Bolm. "Enantioselective Organocatalytic Synthesis of Quaternary α-Amino Acids Bearing a CF3Moiety". Organic Letters 13, № 5 (2011): 1044–47. http://dx.doi.org/10.1021/ol103093r.

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17

Gómez, José Enrique, Wusheng Guo, Silvia Gaspa та Arjan W. Kleij. "Corrigendum: Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters". Angewandte Chemie International Edition 56, № 51 (2017): 16111. http://dx.doi.org/10.1002/anie.201711781.

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18

Bera, Kalisankar, та Irishi N. N. Namboothiri. "Asymmetric Synthesis of Quaternary α-Amino Acids and Their Phosphonate Analogues". Asian Journal of Organic Chemistry 3, № 12 (2014): 1234–60. http://dx.doi.org/10.1002/ajoc.201402178.

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19

Enders, Dieter, Katharina Gottfried та Gerhard Raabe. "Organocatalytic Enantioselective Strecker Synthesis of α-Quaternary α-Trifluoromethyl Amino Acids". Advanced Synthesis & Catalysis 352, № 18 (2010): 3147–52. http://dx.doi.org/10.1002/adsc.201000666.

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20

Gómez, José Enrique, Wusheng Guo, Silvia Gaspa та Arjan W. Kleij. "Berichtigung: Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters". Angewandte Chemie 129, № 51 (2017): 16327. http://dx.doi.org/10.1002/ange.201711781.

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21

Núñez-Villanueva, Diego, Lourdes Infantes, M. Teresa García-López, Rosario González-Muñiz, and Mercedes Martín-Martínez. "Azepane Quaternary Amino Acids As Effective Inducers of 310 Helix Conformations." Journal of Organic Chemistry 77, no. 21 (2012): 9833–39. http://dx.doi.org/10.1021/jo301379r.

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22

Reddy Sanganna Gari, Raghavendar, Patrick Seelheim, Brendan Marsh, Volker Kiessling, Carl Creutz, and Lukas Tamm. "Quaternary Structure of Small Amino Acids Transporter OprG of Pseudomonas aeruginosa." Biophysical Journal 114, no. 3 (2018): 236a—237a. http://dx.doi.org/10.1016/j.bpj.2017.11.1316.

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23

Shu, Shuangjie, Liang Zhao, Shengbin Zhou, Chenglin Wu, Hong Liu та Jiang Wang. "Recyclable and Stable α-Methylproline-Derived Chiral Ligands for the Chemical Dynamic Kinetic Resolution of free C,N-Unprotected α-Amino Acids". Molecules 24, № 12 (2019): 2218. http://dx.doi.org/10.3390/molecules24122218.

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A novel special designed, stable, and recyclable chiral ligand bearing a quaternary carbon was developed for chemical dynamic kinetic resolution (DKR) of free C,N-unprotected racemic α-amino acids via Schiff base intermediates. This method furnishes high yields with excellent enantioselectivity, has a broad substrate scope, and uses operationally simple and convenient conditions. The present chemical DKR is a practical and useful method for the preparation of enantiopure α-amino acids.

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24

Sun, Xi-Shang, Qiu Ou-Yang, Shi-Ming Xu та ін. "Asymmetric synthesis of quaternary α-trifluoromethyl α-amino acids by Ir-catalyzed allylation followed by kinetic resolution". Chemical Communications 56, № 22 (2020): 3333–36. http://dx.doi.org/10.1039/d0cc00845a.

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Facile access to quaternary α-trifluoromethyl α-amino acids has been developed. This sequential reaction involves an Ir-catalyzed asymmetric allylation of α-trifluoromethyl aldimine esters followed by an unprecedented kinetic resolution.

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25

Sun, Xi-Shang, Xing-Heng Wang, Hai-Yan Tao, Liang Wei та Chun-Jiang Wang. "Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement". Chemical Science 11, № 40 (2020): 10984–90. http://dx.doi.org/10.1039/d0sc04685j.

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In this study, we developed an efficient Ir-catalyzed cascade umpolung allylation/2-aza-Cope rearrangement for the preparation of a variety of quaternary trifluoromethyl α-ε-amino acids in high yields with excellent enantioselectivities.

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26

Xue, Zhi-Yong, Zhi-Min Song, and Chun-Jiang Wang. "Cu(i)/TF-BiphamPhos-catalyzed asymmetric Michael addition of cyclic ketimino esters to alkylidene malonates." Organic & Biomolecular Chemistry 13, no. 19 (2015): 5460–66. http://dx.doi.org/10.1039/c5ob00591d.

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Cu(i)-catalyzed asymmetric Michael addition of cyclic ketimino esters with alkylidene malonates has been developed for efficient construction of β-branched α-amino acids containing adjacent quaternary and tertiary stereogenic centers in good yields with excellent diastereo-/enantioselectivities.

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27

Bohnert, Sabine, and Wolf-H. Gündel. "[1.4]Diazepino[6.5-c]chinoline mit L-Aminosäurebaustein — Darstellung und Reaktionen / [1.4]Diazepino[6.5-c]quinolines with L-Amino Acid Moiety — Preparation and Reactions." Zeitschrift für Naturforschung B 42, no. 9 (1987): 1167–73. http://dx.doi.org/10.1515/znb-1987-0918.

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Quaternary salts of the amides of N-(3-quinolinecarbonyl)-N-alkyl-amino acids (6) cyclise under the influence of base to the title compounds (7). This intramolecular addition is a reaction with high diastereoselectivity, dependent on the amino acid part. 7 disproportionates to 8 and 9. 7 behaves as lipophilic NAD model compound in the reaction with 2-propanol under ZnCl2 catalysis.

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28

Cativiela, Carlos, та María D. Díaz-de-Villegas. "Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids". Tetrahedron: Asymmetry 18, № 5 (2007): 569–623. http://dx.doi.org/10.1016/j.tetasy.2007.02.003.

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29

Cativiela, Carlos, та Mario Ordóñez. "Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids". Tetrahedron: Asymmetry 20, № 1 (2009): 1–63. http://dx.doi.org/10.1016/j.tetasy.2009.01.002.

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30

Solà, Jordi, Michael Bolte, and Ignacio Alfonso. "Conformational promiscuity in triazolamers derived from quaternary amino acids mimics peptide behaviour." Organic & Biomolecular Chemistry 13, no. 44 (2015): 10797–801. http://dx.doi.org/10.1039/c5ob01461a.

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31

Roy, Stéphanie, and Claude Spino. "Stereocontrolled Formation of Amino Acids andN-Heterocycles Bearing a Quaternary Chiral Carbon." Organic Letters 8, no. 5 (2006): 939–42. http://dx.doi.org/10.1021/ol053061g.

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32

Trost, Barry M., and Kalindi Dogra. "Synthesis of Novel Quaternary Amino Acids Using Molybdenum-Catalyzed Asymmetric Allylic Alkylation." Journal of the American Chemical Society 124, no. 25 (2002): 7256–57. http://dx.doi.org/10.1021/ja020290e.

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33

Boibessot, Thibaut, David Bénimélis, Patrick Meffre та Zohra Benfodda. "Advances in the synthesis of α-quaternary α-ethynyl α-amino acids". Amino Acids 48, № 9 (2016): 2081–101. http://dx.doi.org/10.1007/s00726-016-2276-2.

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34

Wang, Lei, Abdul Rahman та Xufeng Lin. "Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis". Organic & Biomolecular Chemistry 15, № 28 (2017): 6033–41. http://dx.doi.org/10.1039/c7ob01149k.

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Development of highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids, providing an efficient route to indole-containing chiral cyclic α-amino acid derivatives bearing quaternary stereocenter in high yields and up to 98% enantioselectivity.

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35

Foley, Daniel J., Richard G. Doveston, Ian Churcher, Adam Nelson та Stephen P. Marsden. "A systematic approach to diverse, lead-like scaffolds from α,α-disubstituted amino acids". Chemical Communications 51, № 56 (2015): 11174–77. http://dx.doi.org/10.1039/c5cc03002a.

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A strategy for the efficient lead-oriented synthesis of novel molecular scaffolds is demonstrated. Twenty two scaffolds were prepared from four quaternary α-amino acid building blocks in only 49 synthetic operations, using six connective reactions. The ability of each scaffold to specifically target leadlike chemical space was demonstrated computationally.

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36

Berkowitz, David B., Esmort Chisowa та Jill M. McFadden. "Stereocontrolled synthesis of quaternary β,γ-unsaturated amino acids: chain extension of d- and l-α-(2-tributylstannyl)vinyl amino acids". Tetrahedron 57, № 30 (2001): 6329–43. http://dx.doi.org/10.1016/s0040-4020(01)00499-9.

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37

Undheim, K., Jon Efskind, and G. B. Hoven. "Stereocontrolled construction of conformationally constrained and rigid bis(a-amino acid) derivatives." Pure and Applied Chemistry 75, no. 2-3 (2003): 279–92. http://dx.doi.org/10.1351/pac200375020279.

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Cystine is regarded as a four-atom bridged bis(α-amino acid). The bridge between the two glycine moieties in cystine has been replaced with all-carbon C4-bridges between the α-carbon of the glycines. The products are dicarba analogs of cystine. Conformational constraints have been conferred on these molecules by insertion of cis- and trans- double bonds in the bridge, by alkylidene substituents, by insertion of a triple bond, by insertion of aromatic or heteroaromatic rings, or otherwise by ring formation. Particularly rigidified dicarba analogs of cystine have been prepared where the α-amino

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38

Sanganna Gari, Raghavendar Reddy, Patrick Seelheim, Brendan Marsh, Volker Kiessling, Carl E. Creutz, and Lukas K. Tamm. "Quaternary structure of the small amino acid transporter OprG from Pseudomonas aeruginosa." Journal of Biological Chemistry 293, no. 44 (2018): 17267–77. http://dx.doi.org/10.1074/jbc.ra118.004461.

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Pseudomonas aeruginosa is an opportunistic human pathogen that causes nosocomial infections. The P. aeruginosa outer membrane contains specific porins that enable substrate uptake, with the outer membrane protein OprG facilitating transport of small, uncharged amino acids. However, the pore size of an eight-stranded β-barrel monomer of OprG is too narrow to accommodate even the smallest transported amino acid, glycine, raising the question of how OprG facilitates amino acid uptake. Pro-92 of OprG is critically important for amino acid transport, with a P92A substitution inhibiting transport an

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39

Lyubas, AA, TF Obada, JE Ortiz, et al. "Subfossil freshwater bivalve mollusk shells present data on stratigraphy of Dniester and Prut riverine deposits." Arctic Environmental Research 19, no. 2 (2019): 65–74. http://dx.doi.org/10.3897/issn2541-8416.2019.19.2.65.

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The article provides information on the outcrops of the Neogene-Quaternary riverine sediments of the North-Western Black Sea coastal area. A description of five outcrops of fluvial deposits located on the territory of the modern basins of the Dniester and Prut rivers is given. Based on the granulometric composition of the sediments and the presence in them of the fossil shells of freshwater bivalve mollusks (Bivalvia: Unionoida), an assumption has been made about the characteristics of the ancient river ecosystems of the Dniester and Prut on different Pliocene and Pleistocene time sections. A

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40

Netz, Isabelle, Murat Kucukdisli та Till Opatz. "Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles". Journal of Organic Chemistry 80, № 13 (2015): 6864–69. http://dx.doi.org/10.1021/acs.joc.5b00868.

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41

Di Giacomo, Marcello, Massimo Serra, Marco Brusasca та Lino Colombo. "Stereoselective Pd-Catalyzed Synthesis of Quaternary α-d-C-Mannosyl-(S)-amino Acids". Journal of Organic Chemistry 76, № 13 (2011): 5247–57. http://dx.doi.org/10.1021/jo2002962.

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42

Mosey, Robert A., Jason S. Fisk та Jetze J. Tepe. "Stereoselective syntheses of quaternary substituted α-amino acids using oxazol-5-(4H)-ones". Tetrahedron: Asymmetry 19, № 24 (2008): 2755–62. http://dx.doi.org/10.1016/j.tetasy.2008.11.033.

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43

Enders, Dieter, Katharina Gottfried та Gerhard Raabe. "ChemInform Abstract: Organocatalytic Enantioselective Strecker Synthesis of α-Quaternary α-Trifluoromethyl Amino Acids." ChemInform 42, № 18 (2011): no. http://dx.doi.org/10.1002/chin.201118022.

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44

Cativiela, Carlos, та Maria Dolores Diaz-de-Villegas. "ChemInform Abstract: Stereoselective Synthesis of Quaternary α-Amino Acids. Part 2. Cyclic Compounds". ChemInform 31, № 23 (2010): no. http://dx.doi.org/10.1002/chin.200023253.

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45

Cativiela, Carlos, та Maria Dolores Diaz-de-Villegas. "ChemInform Abstract: Stereoselective Synthesis of Quaternary α-Amino Acids. Part 1. Acyclic Compounds". ChemInform 30, № 10 (2010): no. http://dx.doi.org/10.1002/chin.199910289.

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46

Bera, Kalisankar, та Irishi N. N. Namboothiri. "ChemInform Abstract: Asymmetric Synthesis of Quaternary α-Amino Acids and Their Phosphonate Analogues". ChemInform 46, № 9 (2015): no. http://dx.doi.org/10.1002/chin.201509320.

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47

Volk, Franz-Josef, та August Wilhelm Frahm. "Asymmetric Strecker Synthesis of the Four α-Quaternary 1-Amino-2-methylcyclohexanecarboxylic Acids". Liebigs Annalen 1996, № 11 (1996): 1893–903. http://dx.doi.org/10.1002/jlac.199619961126.

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48

Vachal, Petr, and Eric N. Jacobsen. "Enantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids." Organic Letters 2, no. 6 (2000): 867–70. http://dx.doi.org/10.1021/ol005636+.

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49

Narczyk, Aleksandra, Michał Pieczykolan та Sebastian Stecko. "The synthesis of non-racemic β-alkyl-β-aryl-disubstituted allyl alcohols and their transformation into allylamines and amino acids bearing a quaternary stereocenter". Organic & Biomolecular Chemistry 16, № 21 (2018): 3921–46. http://dx.doi.org/10.1039/c8ob00731d.

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50

Gündel, Wolf-H. "Untersuchungen an quartären Pyridinium-Salzen, XVII Cyclopeptidartige Verbindungen aus Salzen von Nikotinoylaminosäureamiden/Investigations of Quaternary Pyridinium Salts, XVII Cyclopeptide-like Substances from Salts of the Amides of Nicotinoylamino Acids." Zeitschrift für Naturforschung B 40, no. 2 (1985): 305–12. http://dx.doi.org/10.1515/znb-1985-0227.

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Abstract The amides of nicotinoylamino acids were prepared and alkylated to the quaternary salts 1f-n. The α-amino acid moiety in 1 is S configurated. The salts 1 cyclise under the influence of base to give the cyclopeptide-like substances 4, 5 and 7, with seven-or fourteen (sixteen, eighteen-) membered rings, respectively.

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