Oligosaccharide profiling: the facile detection of mono-, di- and oligosaccharides by electrospray orthogonal time-of-flight mass spectrometry using 3-aminophenylboronic acid derivatization

Williams, Dudley; Lee, Terry D.; Dinh, Nikita; Young, Mary K.

doi:10.1002/1097-0231(20000830)14:16<1530::aid-rcm59>3.0.co;2-3

Cited by 13 publications

(9 citation statements)

References 29 publications

(30 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Introducing ionizable nitrogen into the structures of poorly ionizable drugs or drug metabolites is a useful strategy to improve the detection sensitivity. Diol containing compounds such as carbohydrates can be derivatized using 3-aminophenylboronic acid to increase ionization efficiency [100]. Fatty acids can be converted to quaternary ammonium salts by derivatization as alkyldimethylaminoethyl ester iodides for better ionization in qualitative and quantitative LC-MS analysis [101].…”

Section: Chemical Derivatizationmentioning

confidence: 99%

Application of Mass Spectrometry for Metabolite Identification

Ma¹,

Chowdhury²,

Alton³

2006

CDM

143

100

View full text Add to dashboard Cite

Metabolism studies play a pivotal role in drug discovery and development. Characterization of metabolic "hot-spots" as well as reactive and pharmacologically active metabolites is critical to designing new drug candidates with improved metabolic stability, toxicological profile and efficacy. Metabolite identification in the preclinical species used for safety evaluation is required in order to determine whether human metabolites have been adequately tested during non-clinical safety assessment. From an instrumental standpoint, high performance liquid chromatography (HPLC) coupled with mass spectrometry (MS) dominates all analytical tools used for metabolite identification. The general strategies employed for metabolite identification in both drug discovery and drug development settings together with sample preparation techniques are reviewed herein. These include a discussion of the various ionization methods, mass analyzers, and tandem mass spectrometry (MS/MS) techniques that are used for structural characterization in a modern drug metabolism laboratory. Mass spectrometry-based techniques, such as stable isotope labeling, on-line H/D exchange, accurate mass measurement to enhance metabolite identification and recent improvements in data acquisition and processing for accelerating metabolite identification are also described. Rounding out this review, we offer additional thoughts about the potential of alternative and less frequently used techniques such as LC-NMR/MS, CRIMS and ICPMS.

show abstract

Section: Chemical Derivatizationmentioning

confidence: 99%

Application of Mass Spectrometry for Metabolite Identification

Ma¹,

Chowdhury²,

Alton³

2006

CDM

143

100

View full text Add to dashboard Cite

show abstract

“…They used the coordination of ligand toward the target molecule with non‐covalent bond like the adduction of cations (e. g. proton) during the usual ionization process, and performed the observation of complexes with innate polarity in positive mode. Furthermore, Young and Pohl reported the identification of monosaccharide‐3‐aminophenyl boronic acid complexes by MS/MS analysis, but their complexes were linked by a covalent bond, and were observed as protonated trigonal boronates in the positive ion mode.…”

Section: Figurementioning

confidence: 99%

Binding Assessment of Monosaccharide–Boronic Acid Complexes via Tandem Mass Spectrometry

2018

View full text Add to dashboard Cite

Benzoxaborole and arylboronic acids bind to monosaccharides in water to form reversible boronic esters with multiple hydroxyl groups. When benzoxaborole binds with a diol or an arylboronic acid binds with a triol on a monosaccharide, a tetrahedral boron anion is formed at the boron atom. These boron anions can be detected as negative ions in mass spectrometry and tandem mass spectrometry, and profiling their fragment anions provides information on the stereo‐ and regiochemical configurations of the hydroxyl groups on the monosaccharides. Borate fragment anions derived from both benzoxaborole and arylboronic acids show differential connections with hydroxyl groups, which reflect the steric structure of the monosaccharide. As the result, we could distinguish monosaccharides by using the differences in the binding abilities of monosaccharide‐boronic acid complexes by means of mass spectrometric analysis.

show abstract

“…As a matter of fact, there are several examples of boronic acid binding to diols/hydroxyl groups on six-membered rings [5,58,91,92]. Furthermore, immobilized boronic acids have been used to isolate glycans and glycoproteins [93][94][95][96][97][98][99][100][101][102]; free boronic acids have been used for carbohydrate derivatization for mass spectrometric analysis [93,[103][104][105] with much success; SBLs have been used to recognize cell-surface carbohydrate biomarkers which only contain diols on six-membered rings or linear structures [5], and boronic-acid-modified DNA aptamers have been selected to recognize glycoproteins with the ability to differentiate glycosylation variation [57,106]. Such reports lend validity to the use of boronic acids for binding with biologically important carbohydrates that only have hydroxyl groups on six-membered rings.…”

Section: Boronic-acid-based Chemosensorsmentioning

confidence: 99%