Alcoholic beverages, such as wine, beer, and distilled spirits, are widely produced and consumed in different nations. Different types of alcoholic beverages contain different combinations of flavor compounds. However, rapid and simultaneous analysis of a large variety of compounds in alcoholic beverages by a miniatured and portable device remains a challenge. In this paper, a Mycobacterium smegmatis porin A (MspA) nanopore modified with a phenylboronic acid (PBA) adapter is applied for rapid analysis of a variety of alcoholic beverages. By utilizing custom machine learning algorithms, various cis -diols are identified simultaneously in both distilled and fermented alcoholic beverages, generating unique barcodes for each sample type. Nanopore analysis of alcoholic beverages has also never been carried out previously. Rapid grading of wine sweetness and detection of additives, including sucrose and D-tartaric acid, are also demonstrated, showcasing the significance of this technique in the administration of wine production.
cis-Diol-containing metabolites are widely distributed in living organisms, and they participate in the regulation of various important biological activities. The profiling of cis-diol-containing metabolites could help us in fully understanding their functions. In this work, based on the characteristic isotope pattern of boron, we employed a boronic acid reagent as the isotope tag to establish a sensitive and selective liquid chromatography–high-resolution mass spectrometry method for the screening and annotation of cis-diol-containing metabolites in biological samples. Boronic acid reagent 2-methyl-4-phenylaminomethylphenylboronic acid was used to label the cis-diol-containing metabolites in biological samples to improve the selectivity and MS sensitivity of cis-diol-containing metabolites. Based on the characteristic 0.996 Da mass difference of precursor ions and the peak intensity ratio of 1:4 originating from 10B and 11B natural isotopes, the potential cis-diol-containing metabolites were rapidly screened from biological samples. Potential cis-diol-containing metabolites were annotated by database searching and analysis of fragmentation patterns obtained by multistage MS (MSn) via collision-induced dissociation. Importantly, the cis-diol position could be readily resolved by the MS3 spectrum. With this method, a total of 45 cis-diol-containing metabolites were discovered in rice, including monoglycerides, polyhydroxy fatty acids, fatty alcohols, and so forth. Furthermore, the established method showed superiority in avoiding false-positive results in profiling cis-diol-containing metabolites.
Hengye Li,Xuemeng Zhang,Lin Zhang,Xiaojin Wang,Fenying Kong,Dahe Fan,Lei Li,Wei Wang
In this study, a boronate affinity silica stationary phase with enhanced binding properties towards cis -diol compounds was prepared through the combination of surface-initiated atom transfer radical polymerization (SI-ATRP) with a Wulff-type boronate as affinity ligand. The stationary phase showed good hydrophilicity and improved binding strength toward adenosine, with binding constant to be as low as 2.38 × 10 −4 M. The column exhibited excellent binding specificity, low binding pH (≥5.5) and high binding capacities (80.1 μmol adenosine g −1 at pH 7.0 and 45.2 μmol adenosine g −1 at pH 5.5, respectively). The stationary phase was applied as adsorbent for the selective extraction of nucleosides in human urine with excellent specificity and high enrichment efficiency. These results demonstrated that this stationary phase could be favorably applied for selective capture and enrichment of cis -diol compounds in complex samples.
A MALDI-TOF mass spectrometric method is described for the determination
of small molecule compounds with cis-diol. It is based on the use of a binary matrix
consisting of boron nitride (BN) and α-cyano-4-hydroxycinnamic acid that was
modified with the derivatization reagent of (3-(acridin-9-ylamino)phenyl)boronic
acid which can recognize cis-diols. The binary matrix is used for
desorption/ionization (DI) in the positive ion mode. The mechanism leading to DI
enhancement was investigated. The results imply that BN is beneficial for the DI
because it induces an enhancement in the positive ion mode. The boronic
acid-functionalized binary matrix was successfully applied to capture the glucose,
shikimic acid and quinic acid. The method was applied to the determination of
3-chloro-1,2-propanediol in plant oil.
Schematic representation of a method for detecting the
cis-diol compounds on matrix assisted laser desorption/ionization
time-of-flight mass spectrometry (MALDI-TOF MS) using the binary
matrix of boron nitride (BN)/α-cyano-4-hydroxycinnamic acid (CHCA)
that was modified with (3-(acridin-9-ylamino)phenyl) boronic acid
(AYPBA).
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