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1

Ampaw, Anna A., Kayla Newell, and Robert N. Ben. "Investigating the Solubility and Activity of a Novel Class of Ice Recrystallization Inhibitors." Processes 9, no. 10 (2021): 1781. http://dx.doi.org/10.3390/pr9101781.

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O-aryl-β-d-glucosides and N-alkyl-d-gluconamides are two classes of effective ice recrystallization inhibitors (IRIs), however their solubilities limit their use in cryopreservation applications. Herein, we have synthesized and assessed phosphonate analogues of small-molecule IRIs as a method to improve their chemical and physical properties. Four sodium phosphonate compounds 4–7 were synthesized and exhibited high solubilities greater than 200 mM. Their IRI activity was evaluated using the splat cooling assay and only the sodium phosphonate derivatives of α-methyl-d-glucoside (5-Na) and N-oct
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2

Oddon, Y., N. Darbon-Meyssonnier, J. P. Reboul, G. Pepe, E. Decoster, and A. A. Pavia. "N-Benzyl-D-gluconamide." Acta Crystallographica Section C Crystal Structure Communications 42, no. 12 (1986): 1764–66. http://dx.doi.org/10.1107/s0108270186090649.

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3

Müller-Fahrnow, Anke, Wolfram Saenger, Detlef Fritsch, Peter Schnieder, and Jürgen-Hinrich Fuhrhop. "Molecular and crystal structure of the bola-amphiphile N-[8-(d-gluconamido)octyl]-d-gluconamide." Carbohydrate Research 242 (April 1993): 11–20. http://dx.doi.org/10.1016/0008-6215(93)80018-a.

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4

Darbon-Meyssonnier, N., Y. Oddon, E. Decoster, A. A. Pavia, G. Pèpe, and J. P. Reboul. "N-Isopropyl-D-gluconamide (1), C9H19NO6, and N,N-diethyl-D-gluconamide (2), C10H21NO6." Acta Crystallographica Section C Crystal Structure Communications 41, no. 9 (1985): 1324–27. http://dx.doi.org/10.1107/s0108270185007636.

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5

Zhang, Yu-Hui, Ying-Ming Zhang, Jie Yu, Jie Wang, and Yu Liu. "Boronate-crosslinked polysaccharide conjugates for pH-responsive and targeted drug delivery." Chemical Communications 55, no. 8 (2019): 1164–67. http://dx.doi.org/10.1039/c8cc09956a.

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6

Zhang, Xun, Jinguo Liu, Yuxia Gao, Jie Hao, Jun Hu, and Yong Ju. "Multi-stimuli-responsive hydrogels of gluconamide-tailored anthracene." Soft Matter 15, no. 23 (2019): 4662–68. http://dx.doi.org/10.1039/c9sm00656g.

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Two gluconamide-tailored anthracene gelators 1 and 2 were found to form stable hydrogels which exhibited multiple responsive behaviours upon exposure to temperature, anions, light, electron-deficient chemicals and external stress.
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7

Zhang, Dian Long, Guiyun Zhong, Guoyong Wang, and Guojin Li. "Synthesis and Properties of Gluconamide-Based Trisiloxane Surfactant." Journal of Dispersion Science and Technology 33, no. 11 (2012): 1603–7. http://dx.doi.org/10.1080/01932691.2011.629500.

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8

Fuhrhop, Juergen-Hinrich, Dragan Spiroski, and Peter Schnieder. "Two polymeric micellar fibers with gluconamide head groups." Reactive Polymers 15 (November 1991): 215–20. http://dx.doi.org/10.1016/0923-1137(91)90166-l.

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9

Hafkamp, Rudi J. H., Martinus C. Feiters, and Roeland J. M. Nolte. "Tunable Supramolecular Structures from a Gluconamide Containing Imidazole." Angewandte Chemie International Edition in English 33, no. 9 (1994): 986–87. http://dx.doi.org/10.1002/anie.199409861.

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10

Fenimore, Stephen G., Ludmila Abezgauz, Dganit Danino, Chia-Chi Ho, and Carlos C. Co. "Spontaneous Alternating Copolymer Vesicles of Alkylmaleimides and Vinyl Gluconamide." Macromolecules 42, no. 7 (2009): 2702–7. http://dx.doi.org/10.1021/ma802472j.

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11

Tao, Lei. "Thermodynamics Properties of Micellization of Organosilicone Modified Gluconamide-Type Surfactant." Asian Journal of Chemistry 25, no. 17 (2013): 9865–68. http://dx.doi.org/10.14233/ajchem.2013.15527.

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12

Zhi, Lifei, Qiuxiao Li, Yongqiang Sun, and Shushan Yao. "Mixed Stability and Antimicrobial Properties of Gluconamide-Type Cationic Surfactants." Journal of Surfactants and Detergents 19, no. 2 (2016): 337–42. http://dx.doi.org/10.1007/s11743-015-1773-8.

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13

Braunmühl, V. von, R. Stadler, and D. Schollmeyer. "Crystal structure of 2,3,4,5,6-pentaacetyl-(N-allyl)-D-gluconamide, C19H27NO11." Zeitschrift für Kristallographie - New Crystal Structures 213, no. 1-4 (1998): 421–23. http://dx.doi.org/10.1524/ncrs.1998.213.14.421.

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14

Sakai, Kenichi, Shin Umezawa, Mamoru Tamura, et al. "Adsorption and micellization behavior of novel gluconamide-type gemini surfactants." Journal of Colloid and Interface Science 318, no. 2 (2008): 440–48. http://dx.doi.org/10.1016/j.jcis.2007.10.039.

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15

Iftikhar, Mehwish, Lin Wang, and Zhijie Fang. "Synthesis of 1-Deoxynojirimycin: Exploration of Optimised Conditions for Reductive Amidation and Separation of Epimers." Journal of Chemical Research 41, no. 8 (2017): 460–64. http://dx.doi.org/10.3184/174751917x15000341607489.

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1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra- O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra- O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenoly
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16

Zhi, Lifei, Qiuxiao Li, Yunling Li, Yongbo Song, and Ping Li. "Effect of Borax on the Solubility of Dicephalic Gluconamide-Type Surfactants." Journal of Dispersion Science and Technology 34, no. 11 (2013): 1535–39. http://dx.doi.org/10.1080/01932691.2012.752329.

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17

Misiak, Paweł, Kazimiera A. Wilk, Teresa Kral, et al. "New gluconamide-type cationic surfactants: Interactions with DNA and lipid membranes." Biophysical Chemistry 180-181 (October 2013): 44–54. http://dx.doi.org/10.1016/j.bpc.2013.06.010.

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18

Zhi, Lifei, Junyan Li, Xiaoming Li, et al. "Enhancing water solubility of N-dodecyl-d-gluconamide surfactant using borax." Chemical Physics Letters 725 (June 2019): 87–91. http://dx.doi.org/10.1016/j.cplett.2019.04.003.

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19

Xu, Tiantian, Weiqi Liu, Zhi Li, et al. "Photothermal and selective microbial inactivation behaviors of gluconamide-coated IR780 nanoparticles." Colloids and Surfaces B: Biointerfaces 222 (February 2023): 113126. http://dx.doi.org/10.1016/j.colsurfb.2023.113126.

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20

Svenson, Soenke, Juergen Koening, and Juergen Hinrich Fuhrhop. "Crystalline order in probably hollow micellar fibers of N-octyl-D-gluconamide." Journal of Physical Chemistry 98, no. 3 (1994): 1022–28. http://dx.doi.org/10.1021/j100054a045.

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21

Sun, Shengtong, and Peiyi Wu. "Spectral insights into gelation microdynamics of N-octyl-D-gluconamide in water." Soft Matter 7, no. 14 (2011): 6451. http://dx.doi.org/10.1039/c1sm05548h.

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22

Messerschmidt, Christian, Sönke Svenson, Wolfgang Stocker, and Jürgen-Hinrich Fuhrhop. "Rearrangements ofN-Octyl-d-gluconamide Fibers and Bilayers on Gold and Silicon Surfaces." Langmuir 16, no. 19 (2000): 7445–48. http://dx.doi.org/10.1021/la0002684.

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23

Smith, Steven, Liladhar Paudel, Crystal Cyrus, et al. "Sugar-Functional Vinyl Addition Poly(norbornene)–Photopatternable Poly(norbornenyl gluconamide) Compositions Developed with Water." ACS Omega 3, no. 3 (2018): 2909–17. http://dx.doi.org/10.1021/acsomega.8b00081.

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24

Zhou, Xiyang, Yanyun Bai, Lingxiao Guo, and Guoyong Wang. "Effect of siloxane backbone length on the physicochemical properties of gluconamide-modified polysiloxane surfactants." Journal of Molecular Liquids 311 (August 2020): 113355. http://dx.doi.org/10.1016/j.molliq.2020.113355.

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25

Müller-Fahrnow, Anke, Rolf Hilgenfeld, Holger Hesse, Wolfram Saenger, and Beate Pfannemüller. "Molecular and crystal structures of N-(n-heptyl)- and N-(n-decyl)-d-gluconamide." Carbohydrate Research 176, no. 2 (1988): 165–74. http://dx.doi.org/10.1016/0008-6215(88)80128-9.

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26

Jeffrey, George A., and Hanna Maluszynska. "The crystal structure and thermotropic liquid-crystal properties of N-n-undecyl-d-gluconamide." Carbohydrate Research 207, no. 2 (1990): 211–19. http://dx.doi.org/10.1016/0008-6215(90)84049-z.

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27

Dill, Kilian, Marsha E. Daman, Elaine Decoster, Jean M. Lacombe, and André A. Pavia. "Stereochemistry of Gd3+ and Mn2+ interactions with D-gluconamide derivatives by 13C NMR spectroscopy." Inorganica Chimica Acta 106, no. 4 (1985): 203–8. http://dx.doi.org/10.1016/s0020-1693(00)82270-7.

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28

Yoo, Mi Kyong, In Yong Kim, Eun Mi Kim, et al. "Superparamagnetic Iron Oxide Nanoparticles Coated with Galactose-Carrying Polymer for Hepatocyte Targeting." Journal of Biomedicine and Biotechnology 2007 (2007): 1–9. http://dx.doi.org/10.1155/2007/94740.

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Our goal is to develop the functionalized superparamagnetic iron oxide nanoparticles (SPIONs) demonstrating the capacities to be delivered in liver specifically and to be dispersed in physiological environment stably. For this purpose, SPIONs were coated with polyvinylbenzyl-O-β-D-galactopyranosyl-D-gluconamide (PVLA) having galactose moieties to be recognized by asialoglycoprotein receptors (ASGP-R) on hepatocytes. For use as a control, we also prepared SPIONs coordinated with 2-pyrrolidone. The sizes, size distribution, structure, and coating of the nanoparticles were characterized by transm
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29

Yoshimura, Tomokazu, and Kanae Nyuta. "Dynamic Surface Tension of Heterogemini Surfactants with Quaternary Ammonium Salt and Gluconamide or Sulfobetaine Headgroups." Journal of Oleo Science 66, no. 10 (2017): 1139–47. http://dx.doi.org/10.5650/jos.ess17021.

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30

Różycka-Roszak, Bożenna, Paweł Misiak, Edyta Woźniak, Ewa Zaczyńska, Anna Czarny, and Kazimiera A. Wilk. "Effect of biocompatible gluconamide-type cationic surfactants on thermotropic phase behavior of phosphatidylcholine/cholesterol bilayers." Thermochimica Acta 590 (August 2014): 219–25. http://dx.doi.org/10.1016/j.tca.2014.07.005.

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31

Różycka-Roszak, Bożenna, Edyta Woźniak, Paweł Misiak, Renata Frąckowiak, and Kazimiera A. Wilk. "Thermodynamic properties of new gluconamide-based cationic surfactants in aqueous solution: Experimental and modeling approaches." Journal of Chemical Thermodynamics 66 (November 2013): 1–8. http://dx.doi.org/10.1016/j.jct.2013.06.012.

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32

Zhi, Lifei, Qiuxiao Li, Yunling Li, and Yongbo Song. "Adsorption and aggregation properties of novel star-shaped gluconamide-type cationic surfactants in aqueous solution." Colloid and Polymer Science 292, no. 5 (2014): 1041–50. http://dx.doi.org/10.1007/s00396-013-3147-y.

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33

Sack, I., S. Macholl, J. H. Fuhrhop, and G. Buntkowsky. "Conformational studies of polymorphic N-octyl-D-gluconamide with 15N (labeled) 13C (natural abundance) REDOR spectroscopy." Physical Chemistry Chemical Physics 2, no. 8 (2000): 1781–88. http://dx.doi.org/10.1039/a909713i.

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34

Candel, Inmaculada, Elena Aznar, Laura Mondragón, et al. "Amidase-responsive controlled release of antitumoral drug into intracellular media using gluconamide-capped mesoporous silica nanoparticles." Nanoscale 4, no. 22 (2012): 7237. http://dx.doi.org/10.1039/c2nr32062b.

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35

Svenson, Sönke. "EM studies of long-lived fiber gels complemented by solid state 2H-NMR spectroscopy." Proceedings, annual meeting, Electron Microscopy Society of America 48, no. 4 (1990): 852–53. http://dx.doi.org/10.1017/s0424820100177398.

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Aqueous gels (1%) consisting of the amphiphilic N-octyl-D- gluconamide (D-Glu-8) usually crystallize within a few hours.They remain stable for more than five months if 0.4% of sodium dodecylsulfate (SDS) is added. It was shown by electron microscopy that the gels are formed by helical fibers of at least bimolecular thickness (4 nm) and of several micrometers length. Randomly dispersed particles with a mean diameter of 5 nm, which are assumed as micelles, were also observed on micrographs (Fig.1).To provide evidence for this assumption and to rule out the possibility of artefacts introduced by
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36

Herbst, Roswitha, Thomas Steiner, Beate Pfannemüller, and Wolfram Saenger. "Crystal and molecular structure of N-(n-octyl)-6-deoxy-d-gluconamide: a novel packing of amphiphilic molecules." Carbohydrate Research 269, no. 1 (1995): 29–41. http://dx.doi.org/10.1016/0008-6215(94)00346-h.

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37

Ahn, Chang Hyun, Young Jin Kim, Inn Kyu Kang, et al. "High Hepatic Function Was Maintained on Electrospun Nanofibrous Scaffold." Key Engineering Materials 342-343 (July 2007): 197–200. http://dx.doi.org/10.4028/www.scientific.net/kem.342-343.197.

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In this study, we prepared polystyrene (PS) nanofibers as hepatocytes culture substrates by electrospinning method and subsequently coated with specific ligand (poly(N--vinylbenzyl-- β-D-galactopyranosyl-(14)-D-gluconamide)(PVLA) for hepatocytes attachment. Rat hepatocytes’ behavior on the PVLA-coated and non-coated PS nanofibrous matrices have been investigated. Electrospun PS fiber structures revealed randomly aligned fibers with average diameter of 500 nm. Fabricated PS nanofibers had no bonding points like cotton fibers. Analyses by ATR/FTIR and ESCA revealed that PVLA was successfully coa
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38

Goto, Mitsuaki, Yoshiyuki Makino, Kazukiyo Kobayashi, Chong-Su Cho та Toshihiro Akaike. "Hepatocyte attachment onto thermosensitive poly(N-isopropylacrylamide co-N-p-vinylbenzyl-O -β-D-galactopyranosyl(1 → 4)-D-gluconamide)". Journal of Biomaterials Science, Polymer Edition 12, № 7 (2001): 755–68. http://dx.doi.org/10.1163/156856201750411648.

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39

Wang, Jinn Lung, Leslie Leiserowitz, and Meir Lahav. "A correlation between surface wettability and solvent effect on crystal growth. The N-n-octyl-D-gluconamide/methanol system." Journal of Physical Chemistry 96, no. 1 (1992): 15–16. http://dx.doi.org/10.1021/j100180a006.

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40

Bae, Jin Suk, Ga Young Jun, Akihiko Kikuchi, et al. "A Novel Cell Co-Culture Method Utilizing Thermo-Responsive Surface." Key Engineering Materials 342-343 (July 2007): 221–24. http://dx.doi.org/10.4028/www.scientific.net/kem.342-343.221.

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In this work, we developed a novel patterned co-culture method with thermo-responsive poly(N-isopropylacrylamide) (PIPAAm) and poly(N-ρ-vinylbenzyl-Ο-β-D-galactopyranosyl-(1→ 4)-D-gluconamide) (PVLA) inducing active hepatocyte attachment. Patterned graft of PIPAAm onto PS dishes was carried out by electron beam irradiation using cover-glass as a photomask. PVLA was only coated onto PIPAAm-ungrafted domain because of hydrated hydrophilic property of PIPAAm at below the LCST. Analysis by attenuated total reflection-Fourier transform infrared and electron spectroscopy for chemical analysis reveal
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41

Watanabe, Yoshifumi, Xin Liu, Isao Shibuya та Toshihiro Akaike. "Functional evaluation of poly-(N-ρ-vinylbenzyl-O-β-Dgalactopyranosyl-[1-4]-D-gluconamide)(PVLA) as a liver specific carrier". Journal of Biomaterials Science, Polymer Edition 11, № 8 (2000): 833–48. http://dx.doi.org/10.1163/156856200744048.

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42

Yabuuchi, Kazuhiro, Alan E. Rowan, Roeland J. M. Nolte, and Takashi Kato. "Liquid-Crystalline Physical Gels: Self-Aggregation of a Gluconamide Derivative in Mesogenic Molecules for the Formation of Anisotropic Functional Composites." Chemistry of Materials 12, no. 2 (2000): 440–43. http://dx.doi.org/10.1021/cm9904887.

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43

Takei, R., S. J. Seo, C. S. Cho, Y. Okahata та T. Akaike. "Adsorption behaviors of poly(N-p-vinylbenzyl-4-o-β-d-galactopyranosyl-[1→4]-d-gluconamide) by quartz-crystal microbalance". Colloids and Surfaces B: Biointerfaces 42, № 2 (2005): 137–40. http://dx.doi.org/10.1016/j.colsurfb.2005.02.004.

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44

Ueda, Masato, Masato Nishimura, and Norio Miyaura. "ChemInform Abstract: A Palladium-Catalyzed Biaryl Coupling of Arylboronic Acids in Aqueous Media Using a Gluconamide-Substituted Triphenylphosphine (GLCAphos) Ligand." ChemInform 31, no. 41 (2000): no. http://dx.doi.org/10.1002/chin.200041043.

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45

Lakshmi Praveen, P., and Durga P. Ojha. "Estimation of Configurational Probability and Phase Behaviour of N-n-undecyl-D-gluconamide having V-Shaped Conformation – A Molecular Simulation Approach." Zeitschrift für Naturforschung A 67, no. 3-4 (2012): 210–16. http://dx.doi.org/10.5560/zna.2011-0067.

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The present article deals with the configurational probabilities of a smectogen N-n-undecyl-Dgluconamide (GAM11). The complete neglect differential overlap (CNDO/2) method has been employed to compute the net atomic charge and atomic dipole moment components at each atomic center. The modified Rayleigh-Schr¨odinger perturbation theory along with the multicentered-multipole expansion method has been employed to evaluate the long-range intermolecular interactions, while a ‘6-exp’ potential function has been assumed for short-range interactions. The total interaction energy values obtained during
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46

Yoshinaga, Naoto, Takehiko Ishii, Mitsuru Naito, et al. "Polyplex Micelles with Phenylboronate/Gluconamide Cross-Linking in the Core Exerting Promoted Gene Transfection through Spatiotemporal Responsivity to Intracellular pH and ATP Concentration." Journal of the American Chemical Society 139, no. 51 (2017): 18567–75. http://dx.doi.org/10.1021/jacs.7b08816.

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47

Khoshkhoo, Sohrab, та Jamshed Anwar. "Study of the effect of solvent on the morphology of crystals using molecular simulation: application to α-resorcinol and N-n-octyl-D-gluconamide". J. Chem. Soc., Faraday Trans. 92, № 6 (1996): 1023–25. http://dx.doi.org/10.1039/ft9969201023.

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48

Ganewatta, Nisansala, and Ziad El Rassi. "Poly(glyceryl monomethacrylate-co-ethylene glycol dimethacrylate) monolithic columns with incorporated bare and surface modified gluconamide fumed silica nanoparticles for hydrophilic interaction capillary electrochromatography." Talanta 179 (March 2018): 632–40. http://dx.doi.org/10.1016/j.talanta.2017.11.062.

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49

André, Christoph, Peter Luger, and Sönke Svenson. "The crystal packing of N-(n-octyl)-d-gulonamide containing tail-to-tail sheets compared to its gluconamide diastereomer showing head-to-tail arrangement." Carbohydrate Research 230, no. 1 (1992): 31–40. http://dx.doi.org/10.1016/s0008-6215(00)90511-1.

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50

André, Christoph, Peter Luger, Thomas Gutberlet, Dieter Vollhardt, and Jürgen-Hinrich Fuhrhop. "The X-ray crystal structure of N-(1-hexadecyl)-d-gluconamide and powder diffraction studies on its lower and higher homologues (n = 9−18)." Carbohydrate Research 272, no. 2 (1995): 129–40. http://dx.doi.org/10.1016/0008-6215(94)00011-4.

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