Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• previous studies [31][33][34][37][46], solutions of sialyl donors 1 and 2 in the reaction solvent (MeCN) by polarimetry, which is known [31][33][34][35][37][46][57][60][61][62][63] to be highly sensitive to changes in the structure of solutions. Analysis of the concentration dependence of the specific

• outcome. Although polarimetry data clearly suggest, in our opinion, the presence of different supramers in solutions of glycosyl donors 1 and 2 with different concentrations at ambient temperature (28 °C) (Figure 1, Table 1), the situation may be different at much lower temperatures (≤−40 °C), at which

• additional physicochemical studies were attempted to support our rationalization, which is based on polarimetry data only (polarimetry is currently “the method of choice for supramer analysis of solutions” due to its exceptional sensitivity to changes in solution structure [60][61][62][63]), previous

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

• Alexander Dahlqvist,
• Axel Furevi,
• Niklas Warlin,
• Hakon Leffler and
• Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

• , 0.25 s every 30 s, average 3. For optical rotation measurements, samples were dissolved in an appropriate solvent to a concentration of 2–10 mg/mL. Polarimetry was performed on a PerkinElmer Model 341 Polarimeter using a sodium lamp and measuring at 589 nM with a 90 mm long 1 mL cell at 20 °C. For

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• applications in biological systems, such as vectors for simultaneous drug and gene cellular uptake or alternatively for the protection of macromolecules. In particular, we exploited polarimetry to test their interaction with some model p-nitroaniline derivatives, chosen as probe guests. The data obtained

• our materials to exploit both the cavity and the polycationic branches, thus functioning as bimodal ligands. Keywords: aminocyclodextrins; binding properties; nitroanilines; pDNA; polarimetry; supramolecular chemistry; Introduction Polyamine macromolecules have attracted a widespread interest for

• inclusion properties of the main CD scaffold. At the same time, we wanted to clarify the microscopic features and quantitative aspects of the interaction between AmCDs and polyanions such as polynucleotides. For these purposes, we investigated by means of polarimetry the behaviour of materials CD1–CD3

Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

• Polarimetry was used to investigate the binding abilities of a chiral calix[4]resorcinarene derivative, bearing L-proline subunits, towards a set of suitably selected organic guests. The simultaneous formation of 1:1 and 2:1 host–guest inclusion complexes was observed in several cases, depending on both the

• interactions, π–π interactions, desolvation effects and entropy-unfavorable conformational dynamic restraints. Polarimetry is confirmed as a very useful and versatile tool for the investigation of supramolecular interactions with chiral hosts, even in complex systems involving multiple equilibria. Keywords

• : calix[4]resorcinarene; host–guest complexes; p-nitroanilines; polarimetry; supramolecular chemistry; Introduction During the last decades calix[n]arenes and calix[n]resorcinarenes (CAs) have emerged as versatile supramolecular host systems for various applications [1][2][3][4][5], spanning from sensors

One-pot synthesis of block-copolyrotaxanes through controlled rotaxa-polymerization

• Jessica Hilschmann,
• Gerhard Wenz and
• Gergely Kali

Beilstein J. Org. Chem. 2017, 13, 1310–1315, doi:10.3762/bjoc.13.127

• . Since the polymers were soluble in DMSO, the composition could be investigated by polarimetry and 1H NMR spectroscopy (see Table 2) as described in the first part. The 1H NMR spectrum (Figure 2b) of the polymer 4 shows the signals of all RAMEB constituents at 3.0–4.1 and 4.5–5.0 ppm, polyisoprene at 1.0

Characterization of the synthetic cannabinoid MDMB-CHMCZCA

• Carina Weber,
• Stefan Pusch,
• Dieter Schollmeyer,
• Sascha Münster-Müller,
• Michael Pütz and
• Till Opatz

Beilstein J. Org. Chem. 2016, 12, 2808–2815, doi:10.3762/bjoc.12.279

• Ultima 3 instrument (Waters) with a dual electrospray source and an external calibrant. Polarimetry The determination of the optical rotation was carried out at 589 nm and 25 °C in a Perkin-Elmer 241 polarimeter (Perkin Elmer) using a 10 cm path length quartz glass cuvette. Electronic spectroscopy UV and

Chiral recognition of macromolecules with cyclodextrins: pH- and thermosensitive copolymers from N-isopropylacrylamide and N-acryloyl-D/L-phenylalanine and their inclusion complexes with cyclodextrins

• Sabrina Gingter,
• Ella Bezdushna and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 204–209, doi:10.3762/bjoc.7.27

• from 580 D to 1,186 kD. Polarimetry measurements were performed at T = 20 °C in 0.1 N sodium hydroxide solution (λ = 590 nm). Synthesis of D/L-acryloylphenylalanine 2D, 2L 3 g (18 mmol) D/L-phenylalanine were dissolved in 30 mL of sodium hydroxide solution 1.44 g (3.6 mmol) and 1.8 mL (18 mmol) of

• = 2.4 Hz, 17.1 Hz, 1H), 5.60 (dd, J = 2.4 Hz, 9.9 Hz, 1H), 4.53 (J = 4.9 Hz, 9.5 Hz, 1H), 3.12 (dd, J = 4.9 Hz, 13.8 Hz, 1H), 2.91 (dd, J = 9.6 Hz, 13.8 Hz, 1H), Polarimetry: λ = 590 nm, T = 25 °C, 2D [α]D20 = −53, 2L [α]D20 = 53. Elemental analysis: theoretical C 65.7%, N 6.4%, H 6%, found 2D C 65.8

Expanding the gelation properties of valine-based 3,5-diaminobenzoate organogelators with N-alkylurea functionalities

• Hak-Fun Chow and
• Chin-Ho Cheng

Beilstein J. Org. Chem. 2010, 6, 1015–1021, doi:10.3762/bjoc.6.114

• a literature procedure [16], in the presence of N-diisopropylethylamine. Structural characterization All synthesized compounds were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, elemental analysis, and optical polarimetry. Due to the poor solubilities of the