O -Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans
Abstract
Glycoscience has been recognized as an important area in biomedical research. Currently, a major obstacle for glycoscience study is the lack of diverse, biomedically relevant, and complex glycans in quantities sufficient for exploring their structural and functional aspects. Complementary to chemoenzymatic synthesis, natural glycans could serve as a great source of biomedically relevant glycans if they are available in sufficient quantities. We have recently developed oxidative release of natural glycans (ORNG) for large-scale release of N-glycans as free reducing glycans. While free reducing glycans can be readily derivatized with ultraviolet or fluorescent tags for high-performance liquid chromatography (HPLC) and mass spectrometry (MS) analysis, it is difficult to remove tags for the regeneration of free reducing glycans without affecting the structural integrity of glycans. To address this inconvenience, we explored the use of a cleavable tag, O-benzylhydroxylamine (BHA). Free reducing glycans are easily and efficiently labeled with BHA under mild conditions, enabling UV detection during HPLC purification. Individual glycan–BHA conjugates can then be separated using multidimensional HPLC and characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) and MS/MS. The BHA tag can then be easily removed by palladium-on-carbon (Pd/C)-catalyzed hydrogenation to efficiently regenerate free reducing glycans with little effect onmore »
- Authors:
-
- Department of Biochemistry, Emory Comprehensive Glycomics Core, Emory University School of Medicine, Atlanta, GA, USA, Educational Ministry Key Laboratory of Resource Biology and Biotechnology in Western China, College of Life Sciences, Northwest University, Xi’an, China
- Department of Biochemistry, Emory Comprehensive Glycomics Core, Emory University School of Medicine, Atlanta, GA, USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1592786
- Resource Type:
- Published Article
- Journal Name:
- SLAS TECHNOLOGY: Translating Life Sciences Innovation
- Additional Journal Information:
- Journal Name: SLAS TECHNOLOGY: Translating Life Sciences Innovation Journal Volume: 25 Journal Issue: 4; Journal ID: ISSN 2472-6303
- Publisher:
- SAGE Publications
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
Citation Formats
Zhang, Ying, Zhu, Yuyang, Lasanajak, Yi, Smith, David F., and Song, Xuezheng. O -Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans. Country unknown/Code not available: N. p., 2020.
Web. doi:10.1177/2472630319898150.
Zhang, Ying, Zhu, Yuyang, Lasanajak, Yi, Smith, David F., & Song, Xuezheng. O -Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans. Country unknown/Code not available. doi:10.1177/2472630319898150.
Zhang, Ying, Zhu, Yuyang, Lasanajak, Yi, Smith, David F., and Song, Xuezheng. Tue .
"O -Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans". Country unknown/Code not available. doi:10.1177/2472630319898150.
@article{osti_1592786,
title = {O -Benzylhydroxylamine (BHA) as a Cleavable Tag for Isolation and Purification of Reducing Glycans},
author = {Zhang, Ying and Zhu, Yuyang and Lasanajak, Yi and Smith, David F. and Song, Xuezheng},
abstractNote = {Glycoscience has been recognized as an important area in biomedical research. Currently, a major obstacle for glycoscience study is the lack of diverse, biomedically relevant, and complex glycans in quantities sufficient for exploring their structural and functional aspects. Complementary to chemoenzymatic synthesis, natural glycans could serve as a great source of biomedically relevant glycans if they are available in sufficient quantities. We have recently developed oxidative release of natural glycans (ORNG) for large-scale release of N-glycans as free reducing glycans. While free reducing glycans can be readily derivatized with ultraviolet or fluorescent tags for high-performance liquid chromatography (HPLC) and mass spectrometry (MS) analysis, it is difficult to remove tags for the regeneration of free reducing glycans without affecting the structural integrity of glycans. To address this inconvenience, we explored the use of a cleavable tag, O-benzylhydroxylamine (BHA). Free reducing glycans are easily and efficiently labeled with BHA under mild conditions, enabling UV detection during HPLC purification. Individual glycan–BHA conjugates can then be separated using multidimensional HPLC and characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) and MS/MS. The BHA tag can then be easily removed by palladium-on-carbon (Pd/C)-catalyzed hydrogenation to efficiently regenerate free reducing glycans with little effect on glycan structures. This procedure provides a simple and straightforward way to tag free reducing glycans for purification at a preparative scale using multidimensional HPLC and subsequently recover purified free reducing glycans.},
doi = {10.1177/2472630319898150},
journal = {SLAS TECHNOLOGY: Translating Life Sciences Innovation},
number = 4,
volume = 25,
place = {Country unknown/Code not available},
year = {2020},
month = {1}
}
DOI: 10.1177/2472630319898150
Web of Science
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