The stereochemistry of complex formation of polyols with borate and periodate anions, and with metal cations

Angyal, S. J.; Greeves, Diane; Pickles, VA

doi:10.1016/s0008-6215(00)84843-0

Cited by 46 publications

(8 citation statements)

References 19 publications

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“…Later, both the fact of formation of the intermediate complexes and the observance of the first Angyal rule have been confirmed by NMR spectroscopy 127 and paper electrophoresis. 128…”

Section: Complexes With P-metal Cationsmentioning

confidence: 76%

“…2 It was suggested 2 that this process starts with the formation of an unstable complex of the IO À 4 anion with a vicinal diol group; the structure of this complex is similar to that of the tellurate complex 19, because the sizes of the corresponding ions are close. However, monosaccharides conforming to the first Angyal rule should form 127 stable complexes with periodate, for example, a complex of type 20.…”

Section: Complexes With P-metal Cationsmentioning

confidence: 99%

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Complexes of natural carbohydrates with metal cations

Alekseev¹,

Гарновский²,

Zhdanov³

1998

Russ. Chem. Rev.

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Data on the interaction of natural carbohydrates (mono-, oligo-, and poly-saccharides, amino sugars, and natural organic acids of carbohydrate origin) with metal cations are surveyed and described systematically. The structural diversity of carbohydrate metal complexes, caused by some specific features of carbohydrates as ligands, is demonstrated. The influence of complex formation on the chemical properties of carbohydrates is discussed. It is shown that the formation of metal complexes plays an important role in the configurational and conformational analysis of carbohydrates. The practical significance of the coordination interaction in the series of carbohydrate ligands is demonstrated. The bibliography includes 571 references.

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“…Later, both the fact of formation of the intermediate complexes and the observance of the first Angyal rule have been confirmed by NMR spectroscopy 127 and paper electrophoresis. 128…”

Section: Complexes With P-metal Cationsmentioning

confidence: 76%

Section: Complexes With P-metal Cationsmentioning

confidence: 99%

Complexes of natural carbohydrates with metal cations

Alekseev¹,

Гарновский²,

Zhdanov³

1998

Russ. Chem. Rev.

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“…There is not a clear explanation for the positive association between soluble B concentrations and those of DUP and soluble Fe, Al, and Cu. If most of the B is present as borate, it can be speculated that the association with DUP concentrations could be related to the ability of borate to complex with sugar phosphates such as phytic acid (Trevelyan 1967;Angyal, Greeves, and Pickles 1974). Additionally, the high stability constants of the Cu-and Fe-borate complexes (Table 4) suggest that those complexes may have formed.…”

Section: Discussionmentioning

confidence: 99%

Soluble Phosphorus Released by Poultry Wastes in Acidified Aqueous Extracts

Tasistro

Cabrera

Zhao

et al. 2007

Communications in Soil Science and Plant Analysis

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Research has shown that measured water-soluble phosphorus (WSP) from poultry litter might have been less than that released in the field. The effects of acidified extractions on soluble P (SP) concentrations were studied, and a buffer was selected to measure SP at pH 6.0, which is a target value for soil management in Georgia.Soluble P concentrations were extracted from poultry wastes at three pHs: 1) at natural pH, using deionized water (DI w ); 2) after titrating DI w suspensions with 1395 0.5N hydrochloric acid (HCl) to pH end-points 3.0, 4.0, and 6.0; and 3) at pH 6.0 with buffers of sodium (Na) acetate, potassium hydrogen phthalate (KHP), 2-(Nmorpholino) ethanesulphonic acid (MES), Na cacodylate, imidazole, N-(2-acetamido)-2-aminoethansulphonic acid (ACES), N-(carbamoyl-methyl) iminodiacetic acid (ADA), bis-(2-hydroxyethyl) imino]-tris-[(hydroxymethyl) methane (Bistris), and 1,4 piperazine-bis-(ethane sulphonic acid) (PIPES).Total SP increased 60% to 140% in suspensions acidified with HCl to pH 6.0 compared to suspensions at pH ! 8. Dissolved unreactive P responded more (2Â to 30Â) than molybdate reactive P(20 -100%). Buffers extracted more soluble minerals than suspensions acidified with HCl, probably because of their complexation ability. The most effective buffer was MES, because its effects seemed mainly due to acidification.

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“…The reason for the glucose sensitivity of phenylboronic acid is that there are two equilibrium forms of PBA in aqueous solutions: the first is a neutral and hydrophobic form with a planar triangular structure, and the second is a charged and hydrophilic form with a tetrahedral structure . Specific interactions between charged PBA components and cis-glycol compounds (e.g., glucose) can form reversible glucose-boronate complexes, , which can cause the movement of the ionization balance, increase the charge and hydrophilicity, lead to matrix swelling and release payload. − Accordingly, polymers based on PBA in the form of hydrogels, − microgels, − nanogels, , thin films, , micelles, ,, vesicles, , and nanoparticles (NPs) − have been synthesized. Compared to other systems, self-assembled nanoparticles with a core–shell structure have higher drug-loading capacity and drug-loading efficiency, longer circulation time in vivo, greater modifiability, higher bioavailability, etc. , As a result, phenylboronic acid and its derivative-based polymeric nanoparticles as glucose-responsive systems have been actively investigated. ,,,,− Among these PBA-based glucose-responsive systems, block copolymers have drawn much attention for their regular structures and easy self-assembling to core–shell nanoparticles. ,,,− For example, Jin et al synthesized a PBA-based thermoresponsive, glucose-responsive, and pH-responsive block copolymer poly(ethylene oxide)- b -poly(methoxydi(ethylene glycol) methacrylate- co -aminophenylboronic acid ethyl methacrylate) (PEO- b -P(DEGMMA- co -PBAMA)) .…”

Section: Introductionmentioning

confidence: 99%

Glucose-Sensitive Polyphosphoester Diblock Copolymer for an Insulin Delivery System

Zhang

et al. 2020

ACS Biomater. Sci. Eng.

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In this study, we report a diblock copolymer based on a polyphosphate backbone and pendant phenylboronic acid with glucose sensitivity. The copolymer, abbreviated as (PBYP-g-MPBA)-b-PEEP, was prepared via a combination of ring-opening copolymerization, “click” chemistry, and amide reaction, in which the PBYP and PEEP blocks, respectively, represent two kinds of polyphosphoester structures and MPBA represents 3-mercaptopropionic acid modified with 3-aminophenylboronic acid. The amphiphilic copolymer (PBYP-g-MPBA)-b-PEEP could self-assemble into core–shell nanoparticles (NPs) in aqueous solutions. The average particle size and morphology of the NPs were measured by dynamic light scattering and transmission electron microscopy, respectively. The phenomenon that the NPs swelled at different glucose concentrations is due to the formation of boronate esters between the diol groups of glucose and boronic acid groups of phenylboronic acid. Fluorescein isothiocyanate (FITC)–insulin was loaded into the NPs and triggered to release in the presence of glucose. The more the glucose in the release media, the more the FITC–insulin released and the faster the release rate. Methyl thiazolyl tetrazolium assays and hemolysis tests proved that the (PBYP-g-MPBA)-b-PEEP copolymers had good biocompatibility. All of these results verify that the glucose-sensitive polyphosphoester diblock copolymer is highly promising for an insulin delivery system.

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The stereochemistry of complex formation of polyols with borate and periodate anions, and with metal cations

Cited by 46 publications

References 19 publications

Complexes of natural carbohydrates with metal cations

Complexes of natural carbohydrates with metal cations

Soluble Phosphorus Released by Poultry Wastes in Acidified Aqueous Extracts

Glucose-Sensitive Polyphosphoester Diblock Copolymer for an Insulin Delivery System

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