Complexation of boric acid with vitamin C

Köse, Dursun Ali; Zümreoǧlu‐Karan, Birgül

doi:10.1039/b902812a

Cited by 38 publications

(28 citation statements)

References 30 publications

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“…Chemical evidence, X-ray structure solutions, and ab initio studies indicate that the deprotonation involves the proton H3 on the O3 site; see Figure 1. The OH group on C3 has an acidity constant of pK a ∼4.1 to ∼4.25, forming a highly stable AH − mono-anion of ascorbic acid (4,(10)(11)(12)(13)(14)(15)(16)(17). Other tautomers are not so stable; for example, the hydrogen on O2 can be moved to O1, forming a tautomer of ascorbic acid (4), but this is not the only possibility.…”

Section: Introductionmentioning

confidence: 99%

“…Structure clarifications on l-ascorbic acid were later made by infrared (IR) and UV spectroscopy by, for example, Falk and Wojcik (40), Lohmann et al (41,42), and Ferrer and Baran (43). The acid and many salts were studied as solids and in aqueous solutions (also in D 2 O between AgCl windows) by use of IR and 13 C-NMR spectroscopy (17,(34)(35)(36)(37)(41)(42)(43)(44). Panicker et al (45) obtained Fourier transform infrared (FTIR) and FT-Raman spectra including surface-enhanced Raman spectra studies with Ag colloids (probably excited with a 1,064 nm Nd-YAG laser), and many of the vibrational modes of the acid were confirmed or reassigned.…”

Section: Raman Vibrational Spectroscopymentioning

confidence: 99%

“…The most stable di-anion in water solution seems to be obtained by deprotonation of the O2 site or eventually the O6 or O5 sites of the O3 deprotonated ascorbate mono-anion (4); see Figure 1. Formations of these di-anions are rare under physiological conditions requiring a highly basic environment because pK a for the ascorbate mono-anion is ∼11.5 to ∼11.79 (11,14,16,17,19). At even higher basic pH values isomerization at C4 may take place (20).…”

Section: Introductionmentioning

confidence: 99%

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Investigation ofL(+)-Ascorbic acid with Raman spectroscopy in visible and UV light

Berg

2014

Applied Spectroscopy Reviews

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Section: Introductionmentioning

confidence: 99%

Section: Raman Vibrational Spectroscopymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Investigation ofL(+)-Ascorbic acid with Raman spectroscopy in visible and UV light

Berg

2014

Applied Spectroscopy Reviews

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“…11,19,20,54 After complete dissolution of H 3 BO 3 was achieved, NaH 2 PO 4 .2H 2 O was added to the solution containing the mono-ester of the bio-acid. The mixture was gently heated and stirred in a rotary evaporator until complete dissolution.…”

Section: Reaction Conditionsmentioning

confidence: 99%

“…It has been suggested that borate minerals could have played a crucial role by stabilising the cyclic ribose during RNA synthesis. 6−8 A potential and catalytic role of boric acid in peptide and nucleic acid synthesis 9 and stabilisation of sugar molecules by acting as a complexing agent 10,11 have been demonstrated. Recently, thermal condensation of formamide in the presence of borate minerals has been shown to form nucleic acid precursors.…”

Section: Introductionmentioning

confidence: 99%

Organic biomolecules bind to phosphate through borate linkages in aqueous solutions

Aydogmus¹,

Köse²,

Beckett³

et al. 2014

Turk J Chem

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Solutions of salicyclic, ascorbic, and citric acids were reacted with boric acid, followed by NaH 2 PO 4 . The products, triphosphateborate ester of salicylic acid (1), orthosphateborate ester of ascorbic acid (2), triphosphateborate ester of ascorbic acid (3), and orthosphateborate ester of citric acid (4), were flash precipitated with cold acetone and characterised by microanalysis, thermal analysis, FT-IR, Raman, 11 B NMR, 31 P MAS NMR, and mass spectroscopic techniques. Analytical results indicated the presence of -C-O-B-O-P-linkages with the attached phosphate groupsvarying between orthophosphate and triphosphate, depending on the starting material. The biomolecules studied in this work may serve as models in the B-P-organic system and the results would provide a possible contribution to boron prebiotic chemistry.

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Chiral Donor Photoinduced‐Electron‐Transfer (d‐PET) Boronic Acid Chemosensors for the Selective Recognition of Tartaric Acids, Disaccharides, and Ginsenosides

Guo

Zhang

et al. 2011

Chemistry A European J

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A modular approach was proposed for the preparation of chiral fluorescent molecular sensors, in which the fluorophore, scaffold, and chirogenic center can be connected by ethynyl groups, and these modules can easily be changed to other structures to optimize the molecular sensing performance of the sensors. This modular strategy to assembly chiral sensors alleviated the previous restrictions of chiral boronic acid sensors, for which the chirogenic center, fluorophore, and scaffold were integrated, thus it was difficult to optimize the molecular structures by chemical modifications. We demonstrated the potential of our new strategy by the preparation of a sensor with a larger scaffold. The photoinduced electron-transfer (PET) effect is efficient even with a large distance between the N atom and the fluorophore core. Furthermore, the rarely reported donor-PET (d-PET) effect, which was previously limited to carbazole, was extended to phenothiazine fluorophore. The contrast ratio, that is, PET efficiency of the new d-PET sensor, is increased to 8.0, compared to 2.0 with the previous carbazole d-PET sensors. Furthermore, the ethynylated phenothiazine shows longer excitation wavelength (centered at 380 nm) and emission wavelength (492 nm), a large Stokes shift (142 nm), and high fluorescence quantum yield in aqueous solution (Φ=0.48 in MeOH/water, 3:1 v/v). Enantioselective recognition of tartaric acid was achieved with the new d-PET boronic acid sensors. The enantioselectivity is up to 10 (ratio of the binding constants toward D- and L-tartaric acid, k(D)/k(L)). A consecutive fluorescence enhancement/decrease was observed, thus we propose a transition of the binding stoichiometry from 1:1 to 1:2 as the analyte concentration increases, which is supported by mass spectra analysis. The boronic acid sensors were used for selective and sensitive recognition of disaccharides and glycosylated steroids (ginsenosides).

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Complexation of boric acid with vitamin C

Cited by 38 publications

References 30 publications

Investigation ofL(+)-Ascorbic acid with Raman spectroscopy in visible and UV light

Investigation ofL(+)-Ascorbic acid with Raman spectroscopy in visible and UV light

Organic biomolecules bind to phosphate through borate linkages in aqueous solutions

Chiral Donor Photoinduced‐Electron‐Transfer (d‐PET) Boronic Acid Chemosensors for the Selective Recognition of Tartaric Acids, Disaccharides, and Ginsenosides

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