Sugars phenylboronic acid

Horie S, Kubo Y (2009) Fluorescence-based indicator displacement assay for phospho-sugar detection using zinc(II) dipicolylamine-appended phenylboronic acid. Chem Lett 38 616-617... 

Enhancement Factors for Paper-chromatographic Mobility of Free Sugars by Phenylboronic Acid... 

From the known, differential complexing between boronic acids and polyhydroxy compounds, it follows that carbohydrate mixtures may be separated by column-chromatographic methods that exploit the differences. Nucleoside and nucleotide boronates have been separated on columns of anion-exchange resins,90 and sugars and alditols have been shown to be differentially retained on such resins in the sulfonated phenylboronic acid form,64 but perhaps the best uses of column chromatography in this connection have incorporated the resolving powers of insoluble polymers to which boronic acid groups have been covalently bonded. Such insoluble forms of boronates have been synthesized either by substitution of polysaccharide derivatives, or by polymerization of suitable arylboronic acids. 

Different solutions can be applied to avoid the use of polar solvents. The most usual is to make the sugar more lipophilic by introducing hydrophobic groups by simple chemical transformations [56]. In addition, sugars can be solubilized in hydrophobic solvents by in situ complexation with phenylboronic acid [57]. 

Egawa Y, Seki T, Takahashi S et al (2011) Electrochemical and optical sugar sensors based on phenylboronic acid and its derivatives. Mater Sci Eng C 31 1257-1264... 

Purine bases and their nucleosides constitute an important class of antineoplastic and antileukemic agents. Efforts to improve their efficiency in these roles have resulted in the introduction of various structural modifications in both the base and the sugar moiety. Recently, Suzuki reactions of the 6-chloropurine derivative 19 with phenylboronic acids was reported to afford 20 (Equation 45) [54]. 

A study of the stability of compounds derived from D-glucose and D-fructose with boric acid or phenylboronic acid has found that the stability constants for the fructose compounds are much greater than those for the glucose compounds. The synthesis of crystalline 3-0-acetyl-2,4-0-phenylboranediyl- -D-ribopyranosyl bromide in a two pot process from D-ribose has been described along with some of its selective glycosylation reactions. Ethyl (dimethoxy)borane has been used in the synthesis of anomerically pure furanosides from the free sugars. Thus methyl 2,3-0-ethylboranediyl-tt-D-lyxofuranoside was prepared and then de-esterified under essentially neutral conditions to the glycoside in 80%... 

We designed boronic acid fluorescent sensors 3 (n = 1,4) and 4 as supramolecular CD complexes with a sugar recognition functions in which phenylboronic acid and a pyrene fluorophore are connected via a suitable alkyl chain (Figure 13.4). Sensor 3 alone shows weak fluorescence as it rearranges in water, bnt by forming an inclusion... 

The mechanism by which the addition of sugar enhances fluorescence response is shown in Figure 13.4. In this fluorescent sensor, the pyrene fluorophore serves as an electron donor and the phenylboronic acid moiety serves as an electron acceptor. In other words, photo-induced electron transfer (PET) from the donor (pyrene) to the acceptor (acidic or neutral form of phenylboronic acid) causes quenching in the absence of sugar. 

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