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Journal articles on the topic 'Guanidinylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Izawa, Hironori, Mizuki Kinai, Shinsuke Ifuku, Minoru Morimoto, and Hiroyuki Saimoto. "Guanidinylation of Chitooligosaccharides Involving Internal Cyclization of the Guanidino Group on the Reducing End and Effect of Guanidinylation on Protein Binding Ability." Biomolecules 9, no. 7 (2019): 259. http://dx.doi.org/10.3390/biom9070259.

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In order to synthesize a promising material for developing a novel peptide/protein delivery system, guanidinylation of chitooligosaccharides with 1-amidinopyrazole hydrochloride was investigated herein. The production of guanidinylated chitooligosaccharides was demonstrated by infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and elemental analyses. Interestingly, we found that the reducing end in the guanidinylated chitooligosaccharides was converted to a cyclic guanidine structure (2-[(aminoiminomethyl)amino]-2-deoxy-d-glucose structure). This reaction was carefully proven by the

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2

Bolt, H. L., and S. L. Cobb. "A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers." Organic & Biomolecular Chemistry 14, no. 4 (2016): 1211–15. http://dx.doi.org/10.1039/c5ob02279g.

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A practical synthetic procedure to synthesise linear and cyclic peptoids containing both arginine- and lysine-type residues within the same sequence has been developed. The methodology utilises orthogonal N-Boc and N-Dde protection, pyrazole-1-carboxamide as a guanidinylation reagent and is compatible with the sub-monomer method.

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3

Feichtinger, Konrad, Christoph Zapf, Heather L. Sings, and Murray Goodman. "Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents." Journal of Organic Chemistry 63, no. 12 (1998): 3804–5. http://dx.doi.org/10.1021/jo980425s.

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4

FEICHTINGER, K., C. ZAPF, H. L. SINGS, and M. GOODMAN. "ChemInform Abstract: Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents." ChemInform 29, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199845114.

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5

Feichtinger, Konrad, Heather L. Sings, Tracy J. Baker, Kenneth Matthews, and Murray Goodman. "Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions." Journal of Organic Chemistry 63, no. 23 (1998): 8432–39. http://dx.doi.org/10.1021/jo9814344.

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6

Witkowska, Ewa, Karolina Kubik, Jolanta Krosnicka, et al. "Microwave-assisted guanidinylation in solid phase peptide synthesis: comparison of various reagents." Tetrahedron Letters 55, no. 45 (2014): 6198–203. http://dx.doi.org/10.1016/j.tetlet.2014.09.056.

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7

Cortes-Salva, Michelle, Be-Lan Nguyen, Javier Cuevas, Keith R. Pennypacker, and Jon C. Antilla. "Copper-Catalyzed Guanidinylation of Aryl Iodides: The Formation ofN,N′-Disubstituted Guanidines." Organic Letters 12, no. 6 (2010): 1316–19. http://dx.doi.org/10.1021/ol1002175.

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8

Hammoud, Hassan, Martine Schmitt, Frédéric Bihel, Cyril Antheaume, and Jean-Jacques Bourguignon. "Direct Guanidinylation of Aryl and Heteroaryl Halides via Copper-Catalyzed Cross-Coupling Reaction." Journal of Organic Chemistry 77, no. 1 (2011): 417–23. http://dx.doi.org/10.1021/jo202018w.

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9

Mattheis, Claudia, Hui Wang, Claus Meister, and Seema Agarwal. "Effect of Guanidinylation on the Properties of Poly(2-aminoethylmethacrylate)-Based Antibacterial Materials." Macromolecular Bioscience 13, no. 2 (2012): 242–55. http://dx.doi.org/10.1002/mabi.201200217.

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10

Zhao, Xue, Zhen-Zhen Qiao, and Jin-Xin He. "Preparation of Chitosan Biguanidine Hydrochloride and Application in Antimicrobial Finish of Wool Fabric." Journal of Engineered Fibers and Fabrics 5, no. 3 (2010): 155892501000500. http://dx.doi.org/10.1177/155892501000500303.

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Chitosan biguanidine hydrochloride (CGH) has been synthesized by the guanidinylation reaction of chitosan with dicyandiamide. Its synthetic mechanism was discussed. The structures of CGH were characterized by FT-IR and 13CNMR. In this study, we used citric acid (CA) as a crosslinking agent, mixed with CGH to perform a pad-dry-cure treatment on wool fabric to study its antimicrobial effects with the help of scanning electron microscopy (SEM). The result showed that there was no obvious sign that CGH adhered to the wool fabric if the wool fabrics were not oxidized by hydrogen peroxide. The surfa

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11

Maier, Martin A., Isabelle Barber-Peoc'h, and Muthiah Manoharan. "Postsynthetic guanidinylation of primary amino groups in the minor and major grooves of oligonucleotides." Tetrahedron Letters 43, no. 42 (2002): 7613–16. http://dx.doi.org/10.1016/s0040-4039(02)01732-x.

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12

Feichtinger, Konrad, Heather L. Sings, Tracy J. Baker, Kenneth Matthews, and Murray Goodman. "ChemInform Abstract: Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions." ChemInform 30, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199915232.

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13

Cortes-Salva, Michelle, Be-Lan Nguyen, Javier Cuevas, Keith R. Pennypacker, and Jon C. Antilla. "ChemInform Abstract: Copper-Catalyzed Guanidinylation of Aryl Iodides: The Formation of N,N′-Disubstituted Guanidines." ChemInform 41, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.201030085.

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14

Hammoud, Hassan, Martine Schmitt, Frederic Bihel, Cyril Antheaume, and Jean-Jacques Bourguignon. "ChemInform Abstract: Direct Guanidinylation of Aryl and Heteroaryl Halides via Copper-Catalyzed Cross-Coupling Reaction." ChemInform 43, no. 20 (2012): no. http://dx.doi.org/10.1002/chin.201220073.

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15

Lu, Yan Hua, and Ming Su Song. "Effect of Chitosan Biguanidine Hydrochloride on Textile Properties of Antheraea Pernyi Silk." Advanced Materials Research 199-200 (February 2011): 1823–26. http://dx.doi.org/10.4028/www.scientific.net/amr.199-200.1823.

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In order to improve the water-solubility of chitosan, chitosan biguanidine hydrochloride was synthesized by modified chitosan with dicyandiamide in the presence of hydrochloric acid. The guanidinylation chitosan was then applied to Antheraea pernyi (A. pernyi) silk fabric in the presence of 1,2,3,4-butane tetracarboxylic acid with sodium hypophosphite as catalyst. Studies on the effect of chitosan biguanidine hydrochloride treatment on morphology and textile properties of A. pernyi silk fiber and fabric have been conducted. The changes in the morphological structure have been monitored by scan

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16

López-Senín, Paula, Gerard Artigas, and Vicente Marchán. "Exploring the effect of aminoglycoside guanidinylation on ligands for Tau exon 10 splicing regulatory element RNA." Organic & Biomolecular Chemistry 10, no. 46 (2012): 9243. http://dx.doi.org/10.1039/c2ob26623g.

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17

Mamai, Ahmed, and Jose S. Madalengoitia. "Solid-Phase Guanidinylation as a Diversification Strategy of Poly-l-proline Type II Peptide Mimic Scaffolds." Organic Letters 3, no. 4 (2001): 561–64. http://dx.doi.org/10.1021/ol0069711.

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18

Evindar, Ghotas, and Robert A. Batey. "Copper- and Palladium-Catalyzed Intramolecular Aryl Guanidinylation: An Efficient Method for the Synthesis of 2-Aminobenzimidazoles†." Organic Letters 5, no. 2 (2003): 133–36. http://dx.doi.org/10.1021/ol027061h.

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19

Cheng, Qiang, Yuanyu Huang, Hua Zheng, et al. "The effect of guanidinylation of PEGylated poly(2-aminoethyl methacrylate) on the systemic delivery of siRNA." Biomaterials 34, no. 12 (2013): 3120–31. http://dx.doi.org/10.1016/j.biomaterials.2013.01.043.

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20

Baker, T. J., Y. Rew, and M. Goodman. "Novel reagents and reactions for drug design." Pure and Applied Chemistry 72, no. 3 (2000): 347–54. http://dx.doi.org/10.1351/pac200072030347.

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In this presentation, we cover new results from two of our synthetic endeavors: guanidinylation reagents and novel bridged opioids. In the first part, we describe the applications of the diurethane-triflylguanidines to prepare target bioactive structures including peptides, heterocyclic drugs, and aminoglycoside derivatives. The formation of novel guanidinoglycosides led to a family of effective binders to the RNA recognition element of the HIV-1 Rev protein. In the second part, the syntheses of sulfur and amine-bridged cyclic opioids is described. These analogs exhibit enhanced binding, both

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21

Đud, Mateja, Zoran Glasovac, and Davor Margetić. "The utilization of ball milling in synthesis of aryl guanidines through guanidinylation and N-Boc-deprotection sequence." Tetrahedron 75, no. 1 (2019): 109–15. http://dx.doi.org/10.1016/j.tet.2018.11.038.

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22

Zhai, Xinyun, Peng Sun, Yongfeng Luo, Chaonan Ma, Jun Xu, and Wenguang Liu. "Guanidinylation: A simple way to fabricate cell penetrating peptide analogue-modified chitosan vector for enhanced gene delivery." Journal of Applied Polymer Science 121, no. 6 (2011): 3569–78. http://dx.doi.org/10.1002/app.34156.

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23

Bionda, Nina, Jean-Philippe Pitteloud, Jean-Philippe Pitteloud, and Predrag Cudic. "Solid-phase synthesis of fusaricidin/li-f class of cyclic lipopeptides: Guanidinylation of resin-bound peptidyl amines." Biopolymers 100, no. 2 (2013): 160–66. http://dx.doi.org/10.1002/bip.22186.

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24

Li, Jizhen, Yuhua Mi, Jianghua He, Xuyang Luo, and Erkang Fan. "Synthesis of 2-Amino 3-Substituted Quinazolin-4(3H)-one DerivativesviaIodine-Mediated Guanidinylation of Pbf-Activated Thiourea." Journal of Heterocyclic Chemistry 50, no. 2 (2013): 304–8. http://dx.doi.org/10.1002/jhet.1067.

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25

Bionda, Nina, and Predrag Cudic. "ChemInform Abstract: Solid-Phase Guanidinylation of Peptidyl Amines Compatible with Standard Fmoc-Chemistry: Formation of Mono-Substituted Guanidines." ChemInform 46, no. 20 (2015): no. http://dx.doi.org/10.1002/chin.201520315.

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26

Weltrowska, Grazyna, Thi M. D. Nguyen, Nga N. Chung, Brian C. Wilkes, and Peter W. Schiller. "N-terminal guanidinylation of TIPP (Tyr-Tic-Phe-Phe) peptides results in major changes of the opioid activity profile." Bioorganic & Medicinal Chemistry Letters 23, no. 18 (2013): 5082–85. http://dx.doi.org/10.1016/j.bmcl.2013.07.036.

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27

Bańkowski, Krzysztof, Olga M. Michalak, Anna Leśniak, et al. "N -terminal guanidinylation of the cyclic 1,4-ureido-deltorphin analogues: the synthesis, receptor binding studies, and resistance to proteolytic digestion." Journal of Peptide Science 21, no. 6 (2015): 467–75. http://dx.doi.org/10.1002/psc.2762.

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28

Flemer, Stevenson, Alexander Wurthmann, Ahmed Mamai, and José S. Madalengoitia. "Strategies for the Solid-Phase Diversification of Poly-l-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation." Journal of Organic Chemistry 73, no. 19 (2008): 7593–602. http://dx.doi.org/10.1021/jo8012258.

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29

Li, Jizhen, Yuhua Mi, Jianghua He, Xuyang Luo, and Erkang Fan. "ChemInform Abstract: Synthesis of 2-Amino 3-Substituted Quinazolin-4(3H)-one Derivatives via Iodine-Mediated Guanidinylation of Pbf-Activated Thiourea." ChemInform 44, no. 39 (2013): no. http://dx.doi.org/10.1002/chin.201339169.

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30

Kwon, Woong, and Euigyung Jeong. "Detoxification Properties of Guanidinylated Chitosan Against Chemical Warfare Agents and Its Application to Military Protective Clothing." Polymers 12, no. 7 (2020): 1461. http://dx.doi.org/10.3390/polym12071461.

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This study investigates the detoxification properties of guanidinylated chitosan against chemical warfare agents and its application to the preparation of military protective clothing. Guanidinylated chitosan was synthesized by chitosan guanidinylation with cyanamide. The detoxification properties of the guanidinylated chitosan were then evaluated using a chemical warfare agent simulant, called diisopropylfluorophosphate (DFP). Cotton fabric was treated with 1 wt.% of guanidinylated chitosan in acetic acid and water solution using the simple and conventional textile treatment method of pad–dry

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31

Dawadi, Surendra, Nicholas Simmons, Gabriella Miklossy, et al. "Discovery of potent thrombin inhibitors from a protease-focused DNA-encoded chemical library." Proceedings of the National Academy of Sciences 117, no. 29 (2020): 16782–89. http://dx.doi.org/10.1073/pnas.2005447117.

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DNA-encoded chemical libraries are collections of compounds individually coupled to unique DNA tags serving as amplifiable identification barcodes. By bridging split-and-pool combinatorial synthesis with the ligation of unique encoding DNA oligomers, million- to billion-member libraries can be synthesized for use in hundreds of healthcare target screens. Although structural diversity and desirable molecular property ranges generally guide DNA-encoded chemical library design, recent reports have highlighted the utility of focused DNA-encoded chemical libraries that are structurally biased for a

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32

Rueth, M., H. D. Lemke, C. Preisinger, et al. "Guanidinylations of albumin decreased binding capacity of hydrophobic metabolites." Acta Physiologica 215, no. 1 (2015): 13–23. http://dx.doi.org/10.1111/apha.12518.

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33

Qi, Xue Jie, Yuan Lu Cui, Qiang Song Wang та Yun Qi. "Preparation and Characterization of Guanidinylated Chitosan/β-Glycerophosphate Thermo-Sensitive Hydrogel". Advanced Materials Research 749 (серпень 2013): 182–85. http://dx.doi.org/10.4028/www.scientific.net/amr.749.182.

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The purpose of this study was to prepare and characterize guanidinylated chitosan/β-glycerophosphate thermo-sensitive hydrogel system. The primary amine group of chitosan was modified with guanidine group, which was characterized by FT-IR and1H NMR. The results showed that the guanidinylations had been successfully carried out in cyanamide and chitosan. Gelation temperature was modulated at 37 °C with the ratio of 50% β-GP solution (weight/volume) and 4% GCS solution (weight/volume) at pH value ranged from 6.9 to 7.2, which could be development a new drug delivery system at body temperature.

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34

Vera, J., N. Heidi, and J. JANKOWSKI. "SAT-122 Guanidinylations of albumin decreased binding capacity of hydrophobic metabolites." Kidney International Reports 4, no. 7 (2019): S56. http://dx.doi.org/10.1016/j.ekir.2019.05.151.

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35

Musiol, Hans-Jürgen, and Luis Moroder. "N,N‘-Di-tert-butoxycarbonyl-1H- benzotriazole-1-carboxamidine Derivatives Are Highly Reactive Guanidinylating Reagents." Organic Letters 3, no. 24 (2001): 3859–61. http://dx.doi.org/10.1021/ol010191q.

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36

Zapf, Christoph W., Christopher J. Creighton, Mika Tomioka, and Murray Goodman. "A Novel Traceless Resin-Bound Guanidinylating Reagent for Secondary Amines To PrepareN,N-Disubstituted Guanidines." Organic Letters 3, no. 8 (2001): 1133–36. http://dx.doi.org/10.1021/ol015576n.

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37

Musiol, Hans-Juergen, and Luis Moroder. "ChemInform Abstract: N,N′-Di-tert-butoxycarbonyl-1H-benzotriazole-1-carboxamidine Derivatives Are Highly Reactive Guanidinylating Reagents." ChemInform 33, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.200217075.

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38

Schunk, Stefan, Juliane Hermann, Triem Sarah, et al. "MO451GUANIDINYLATED APOLIPOPROTEIN C3 (APOC3) A NOVEL PLAYER IN CKD AND CKD-ASSOCIATED CARDIOVASCULAR DISEASES." Nephrology Dialysis Transplantation 36, Supplement_1 (2021). http://dx.doi.org/10.1093/ndt/gfab090.0013.

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Abstract Background and Aims Cardiovascular diseases (CVD) and chronic kidney diseases (CKD) are highly prevalent in Western populations and account for a substantial proportion of mortality. We found that apolipoprotein C-3 (ApoC3), a constituent of triglyceride-rich lipoproteins, induces alternative NLRP3 inflammasome activation in human monocytes and thus causes sterile inflammation. The aim of the present study was to screen ApoC3 for the presence of posttranslational protein modifications and to assess its relevance in vitro, in vivo, as well as in a prospective cohort of CKD patients. Me

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39

Hermann, Juliane, Ute Raffetseder, Michaela Lellig, Joachim Jankowski, and Vera Jankowski. "MO430MASS-SPECTROMETRIC IDENTIFICATION OF POST-TRANSLATIONAL GUANIDINYLATED PROTEINS IN THE CONTEXT OF SYSTEMIC LUPUS ERYTHEMATOSUS." Nephrology Dialysis Transplantation 36, Supplement_1 (2021). http://dx.doi.org/10.1093/ndt/gfab088.003.

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Abstract Background and Aims With continuous identification of post-translational modified isoforms of proteins, it is becoming increasingly clear that post-translational modifications limit or modify the biological functions of native proteins are majorly involved in development of various chronic disease. This is mostly due to technically advanced molecular identification and quantification methods, mainly based on mass spectrometry. Mass spectrometry has become one of the most powerful tools for the identification of lipids. Method In this study, we used sophisticated high-resolution mass-s

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40

Malmberg, Christopher E., and Stephen Chamberland. "A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products." Journal of Visualized Experiments, no. 115 (September 9, 2016). http://dx.doi.org/10.3791/53593.

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41

Evindar, Ghotas, and Robert A. Batey. "Copper- and Palladium-Catalyzed Intramolecular Aryl Guanidinylation: An Efficient Method for the Synthesis of 2-Aminobenzimidazoles." ChemInform 34, no. 22 (2003). http://dx.doi.org/10.1002/chin.200322116.

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42

Patel, Saurabh. "Non Invasive (Peroral) Delivery System for Glucagon like Peptide - 1 (GLP-1): Site specific Guanidinylation and Biotinylation of Lysine residues in GLP-1 for Treatment of Type II Diabetes." MOJ Toxicology 1, no. 4 (2015). http://dx.doi.org/10.15406/mojt.2015.01.00018.

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43

Patel, Saurabh. "Non Invasive (Peroral) Delivery System for Glucagon like Peptide - 1 (GLP-1): Site specific Guanidinylation and Biotinylation of Lysine residues in GLP-1 for Treatment of Type II Diabetes." MOJ Toxicology 1, no. 4 (2015). http://dx.doi.org/10.15406/mojt.2015.02.00018.

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44

Musiol, Hans-Juergen, and Luis Moroder. "Diurethanyl 1H-Benzotriazole-1-carboxamidines as Guanidinylating Reagents." ChemInform 34, no. 24 (2003). http://dx.doi.org/10.1002/chin.200324255.

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