Merging the Versatile Functionalities of Boronic Acid with Peptides
Peptides inherently feature the favorable properties of being easily synthesized, water-soluble, biocompatible, and typically non-toxic. Thus, boronic acid has been widely integrated with peptides with the goal of discovering peptide ligands with novel biological activities, and this effort has led...
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-11-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/23/12958 |
| _version_ | 1797507737791234048 |
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| author | Yahong Tan Junjie Wu Lulu Song Mengmeng Zhang Christopher John Hipolito Changsheng Wu Siyuan Wang Youming Zhang Yizhen Yin |
| author_facet | Yahong Tan Junjie Wu Lulu Song Mengmeng Zhang Christopher John Hipolito Changsheng Wu Siyuan Wang Youming Zhang Yizhen Yin |
| author_sort | Yahong Tan |
| collection | DOAJ |
| description | Peptides inherently feature the favorable properties of being easily synthesized, water-soluble, biocompatible, and typically non-toxic. Thus, boronic acid has been widely integrated with peptides with the goal of discovering peptide ligands with novel biological activities, and this effort has led to broad applications. Taking the integration between boronic acid and peptide as a starting point, we provide an overview of the latest research advances and highlight the versatile and robust functionalities of boronic acid. In this review, we summarize the diverse applications of peptide boronic acids in medicinal chemistry and chemical biology, including the identification of covalent reversible enzyme inhibitors, recognition, and detection of glycans on proteins or cancer cell surface, delivery of siRNAs, development of pH responsive devices, and recognition of RNA or bacterial surfaces. Additionally, we discuss boronic acid-mediated peptide cyclization and peptide modifications, as well as the facile chemical synthesis of peptide boronic acids, which paved the way for developing a growing number of peptide boronic acids. |
| first_indexed | 2024-03-10T04:52:43Z |
| format | Article |
| id | doaj.art-d10c9628e87146fab326eea995bcd9d2 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T04:52:43Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-d10c9628e87146fab326eea995bcd9d22023-11-23T02:30:57ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-11-0122231295810.3390/ijms222312958Merging the Versatile Functionalities of Boronic Acid with PeptidesYahong Tan0Junjie Wu1Lulu Song2Mengmeng Zhang3Christopher John Hipolito4Changsheng Wu5Siyuan Wang6Youming Zhang7Yizhen Yin8State Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaScreening & Compound Profiling, Quantitative Biosciences, Merck & Co., Inc., Kenilworth, NJ 07033, USAState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaDepartment of Medicinal Chemistry, College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaState Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, ChinaPeptides inherently feature the favorable properties of being easily synthesized, water-soluble, biocompatible, and typically non-toxic. Thus, boronic acid has been widely integrated with peptides with the goal of discovering peptide ligands with novel biological activities, and this effort has led to broad applications. Taking the integration between boronic acid and peptide as a starting point, we provide an overview of the latest research advances and highlight the versatile and robust functionalities of boronic acid. In this review, we summarize the diverse applications of peptide boronic acids in medicinal chemistry and chemical biology, including the identification of covalent reversible enzyme inhibitors, recognition, and detection of glycans on proteins or cancer cell surface, delivery of siRNAs, development of pH responsive devices, and recognition of RNA or bacterial surfaces. Additionally, we discuss boronic acid-mediated peptide cyclization and peptide modifications, as well as the facile chemical synthesis of peptide boronic acids, which paved the way for developing a growing number of peptide boronic acids.https://www.mdpi.com/1422-0067/22/23/12958boronic acidpeptideinhibitorsmolecular recognitionsynthesismodifications |
| spellingShingle | Yahong Tan Junjie Wu Lulu Song Mengmeng Zhang Christopher John Hipolito Changsheng Wu Siyuan Wang Youming Zhang Yizhen Yin Merging the Versatile Functionalities of Boronic Acid with Peptides International Journal of Molecular Sciences boronic acid peptide inhibitors molecular recognition synthesis modifications |
| title | Merging the Versatile Functionalities of Boronic Acid with Peptides |
| title_full | Merging the Versatile Functionalities of Boronic Acid with Peptides |
| title_fullStr | Merging the Versatile Functionalities of Boronic Acid with Peptides |
| title_full_unstemmed | Merging the Versatile Functionalities of Boronic Acid with Peptides |
| title_short | Merging the Versatile Functionalities of Boronic Acid with Peptides |
| title_sort | merging the versatile functionalities of boronic acid with peptides |
| topic | boronic acid peptide inhibitors molecular recognition synthesis modifications |
| url | https://www.mdpi.com/1422-0067/22/23/12958 |
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