The interaction of areneboronic acids with monosaccharides

Barker, S. A.; Chopra, Ashish; Hatt, B.W.; Somers, P.J.

doi:10.1016/s0008-6215(00)85019-3

Cited by 95 publications

(54 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…It is well known that 5-membered rings form a more stable complex [5], but the equilibrium is largely influenced by the geometrical arrangement of the diols. In the other proposed mechanism, a sequential nucleophilic attack of the diol oxygen atoms on the boronic acid causes the formation of the anionic species [6] as shown in equilibrium 3.…”

Section: Some Aspects Of Alkylglncoside-boronate Micellar Phasesmentioning

confidence: 99%

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Smith

Rassi

1994

Electrophoresis

View full text Add to dashboard Cite

This article represents an extension to a new approach introduced very recently by our laboratory for the control of the surface charge density as well as the hydrophobic character of micellar phases used in micellar electrokinetic capillary chromatography (MECC). The approach is based on the complexation of polyolic surfactants, e.g., alkylglucosides, with butylboronate to form in situ branched, anionic surfactants. The butylboronate can also incorporate into the micelle via its alkyl tail and acts as a "class I" organic additive that mainly modifies the micelle by decreasing the critical micellar concentration, i.e., increasing the hydrophobic character of the micelle, while exhibiting little influence on the aqueous phase. The net result is an in situ charged micellar entity whose hydrophobic character is dynamically altered. The alkylglucoside-butylboronate micellar phases yielded high separation efficiencies and proved useful in the separation of charged and neutral herbicides as well as the chiral separations of medicarpins and precursors, and dansylated D and L-amino acids in the presence of native or modified cyclodextrin chiral selectors.

show abstract

Section: Some Aspects Of Alkylglncoside-boronate Micellar Phasesmentioning

confidence: 99%

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Smith

Rassi

1994

Electrophoresis

View full text Add to dashboard Cite

show abstract

“…9 In addition, the interaction of benzeneboronic acid, 4-methoxybenzeneboronic acid and 3-nitrobenzeneboronic acid with D-glucose, D-mannose and D-fructose at various pH values has been investigated by means of optical rotation methods. 10 The interaction of the different boronates with the saccharides is specific depending on the kind of boronic acid and the structure of the saccharide. For example, monosaccharides bearing five OH groups tend to form 1 : 2 monosaccharide-phenylboronic acid complexes.…”

Section: Introductionmentioning

confidence: 99%

Combined ¹H, ¹³C and ¹¹B NMR and mass spectral assignments of boronate complexes of D‐(+)‐glucose, D‐(+)‐mannose, methyl‐α‐D‐glucopyranoside, methyl‐β‐D‐galactopyranoside and methyl‐α‐D‐mannopyranoside

Smoum

Rubinstein

Srebnik

2003

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

show abstract

“…As for the separation in borate, it is well known that borate can generate covalent adducts with cis-diols [10]. On this basis, we hypothesized that borate interacts with the two ribose rings of diadenosine polyphosphates containing a cis-diol couple.…”

Section: Resultsmentioning

confidence: 99%

Separation of diadenosine polyphosphates by capillary electrophoresis

et al. 2000

View full text Add to dashboard Cite

The influence of buffer composition and pH on the electrophoretic behavior of diadenosine polyphosphates with a phosphate chain ranging from two to five phosphate groups has been examined. The electrophoretic mobility in carbonate buffer increases according to the number of phosphates, whereas in borate buffer the mobility changes in an irregular way as a function of pH. This finding can be rationalized by a well-known interaction of borate with ribose rings, which modifies the charge and the hydrodynamic radius of each diadenosine polyphosphate in a different way. Our study shows that the best separation of diadenosine polyphosphates can be achieved at the highest pH values of the range examined both in borate and carbonate buffers.

show abstract

The interaction of areneboronic acids with monosaccharides

Cited by 95 publications

References 9 publications

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Combined ¹H, ¹³C and ¹¹B NMR and mass spectral assignments of boronate complexes of D‐(+)‐glucose, D‐(+)‐mannose, methyl‐α‐D‐glucopyranoside, methyl‐β‐D‐galactopyranoside and methyl‐α‐D‐mannopyranoside

Separation of diadenosine polyphosphates by capillary electrophoresis

Contact Info

Product

Resources

About

The interaction of areneboronic acids with monosaccharides

Cited by 95 publications

References 9 publications

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Micellar electrokinetic capillary chromatography with in situ charged micelles: 3. Evaluation of alkylglucoside surfactants as anionic butylboronate complexes

Combined 1H, 13C and 11B NMR and mass spectral assignments of boronate complexes of D‐(+)‐glucose, D‐(+)‐mannose, methyl‐α‐D‐glucopyranoside, methyl‐β‐D‐galactopyranoside and methyl‐α‐D‐mannopyranoside

Separation of diadenosine polyphosphates by capillary electrophoresis

Contact Info

Product

Resources

About

Combined ¹H, ¹³C and ¹¹B NMR and mass spectral assignments of boronate complexes of D‐(+)‐glucose, D‐(+)‐mannose, methyl‐α‐D‐glucopyranoside, methyl‐β‐D‐galactopyranoside and methyl‐α‐D‐mannopyranoside