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Affinity Chromatography

Catch and Release of Diols with Boronic Acid Agarose

Boronic acids bind diol compounds with high selectivity.[1] Since many biomolecules are diol-decorated sugar derivatives, immobilized boronic acids permit the single step enrichment of

  • Carbohydrates[2]
  • Nucleotides[3]
  • Cofactors[4]
  • Entire Glycoproteins[5] and RNAs[6,7]
To this end, agarose resins stand out for their large exclusion limit (1 x 104 - 4 x 105 Da) and are therefore particularly well suited for the complexation of large biomolecules.[8,9] Capitalizing on the reversibility of boronate ester formation, captured compounds can be easily retrieved under mild conditions for further applications or analysis.

Catch and Release of Diols with Boronic Acid Agarose

Scheme 1: Depending on the pH of the solution, boronic acids coexist in equilibrium with their corresponding boronates (pKa ~ 9). While boronic esters are prone to fast hydrolysis, their tetragonal boronate counterparts are stable and allow for the efficient immobilization of cis-diol functionalities. Trapped diols are then either released by a) lowering the pH or by b) replacement with sorbitol.

Immobilized m-Aminophenylboronic acid offered by Jena Bioscience:

Immobilized m-Aminophenylboronic acid offered by Jena Bioscience

Selected references:
[1] Siegel (2012) Applications of reversible covalent chemistry in analytical sample preparation. Analyst. 137:5457.
[2] Weith et al. (1970) Synthesis of cellulose derivatives containing the dihydroxyboryl group and a study of their capacity to form specific complexes with sugars and nucleic acid components. Biochemistry. 9:4396.
[3] Moore et al. (1974) Separation of ribonucleotides and deoxyribonucleotides on columns of borate covalently linked to cellulose. Application to the assay of ribonucleoside diphosphate reductase. Biochemistry. 13:2904.
[4] Gellekink et al. (2005) Stable-isotope dilution liquid chromatography-electrospray injection tandem mass spectrometry method for fast, selective measurement of S-adenosylmethionine and S-adenosylhomocysteine in plasma. Clin. Chem. 51:1487.
[5] Mallia et. al. (1981) Preparation and use of a boronic acid affinity support for the separation and quantitation of glycosylated hemoglobins. Anal. Lett. 14:649.
[6] Schott et al. (1973) Dihydroxyboryl-substituted methacrylic polymer for the column chromatographic separation of mononucleotides, oligonucleotides, and transfer ribonucleic acid. Biochemistry. 12:932
[7] Nübel et al. (2017) Boronate affinity electrophoresis for the purification and analysis of cofactor-modified RNAs. Methods. 117:14.
[8] Chen et al. (2017) Novel boronate material affords efficient enrichment of glycopeptides by synergized hydrophilic and affinity interactions. Anal. Bioanal. Chem. 409:519.
[9] Grundy et al. (2016) PARP3 is a sensor of nicked nucleosomes and monoribosylates histone H2B(Glu2). Nat. Commun. 7:12404.

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