Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions
The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing...
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| Veröffentlicht in: | Angewandte Chemie International Edition Jg. 60; H. 22; S. 12413 - 12423 |
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Germany
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25.05.2021
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| Ausgabe: | International ed. in English |
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| ISSN: | 1433-7851, 1521-3773, 1521-3773 |
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| Abstract | The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well‐defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.
A so‐called “GlycoComputer” program has been developed to foresee and predict the yield and stereoselectivity of glycosylation reactions based on the properties of various donors, acceptors, activation systems and solvents. The program statistically analyzes and compares the relative reactivity value (RRV) of donors and the acceptor nucleophilic constant (Aka) of acceptors. |
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| AbstractList | The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well‐defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated. The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program "GlycoComputer" for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program "GlycoComputer" for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated. The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well‐defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated. A so‐called “GlycoComputer” program has been developed to foresee and predict the yield and stereoselectivity of glycosylation reactions based on the properties of various donors, acceptors, activation systems and solvents. The program statistically analyzes and compares the relative reactivity value (RRV) of donors and the acceptor nucleophilic constant (Aka) of acceptors. |
| Author | Chang, Chun‐Wei Lin, Mei‐Huei Liao, Pin‐Hsuan Chan, Chieh‐Kai Su, Kuan‐Yu Cheng, Yu‐Ting Lam, Sarah Wang, Cheng‐Chung Wu, Chia‐Hui Lo, Wei‐Chih Wong, Chi‐Huey |
| Author_xml | – sequence: 1 givenname: Chun‐Wei orcidid: 0000-0002-0253-3463 surname: Chang fullname: Chang, Chun‐Wei organization: Academia Sinica – sequence: 2 givenname: Mei‐Huei orcidid: 0000-0002-0842-1964 surname: Lin fullname: Lin, Mei‐Huei organization: Academia Sinica – sequence: 3 givenname: Chieh‐Kai orcidid: 0000-0002-5178-156X surname: Chan fullname: Chan, Chieh‐Kai organization: Academia Sinica – sequence: 4 givenname: Kuan‐Yu surname: Su fullname: Su, Kuan‐Yu organization: Academia Sinica – sequence: 5 givenname: Chia‐Hui orcidid: 0000-0002-5982-136X surname: Wu fullname: Wu, Chia‐Hui organization: Academia Sinica – sequence: 6 givenname: Wei‐Chih orcidid: 0000-0003-3967-4531 surname: Lo fullname: Lo, Wei‐Chih organization: Academia Sinica – sequence: 7 givenname: Sarah surname: Lam fullname: Lam, Sarah organization: Academia Sinica – sequence: 8 givenname: Yu‐Ting orcidid: 0000-0002-0158-8761 surname: Cheng fullname: Cheng, Yu‐Ting organization: Academia Sinica – sequence: 9 givenname: Pin‐Hsuan surname: Liao fullname: Liao, Pin‐Hsuan organization: Academia Sinica – sequence: 10 givenname: Chi‐Huey surname: Wong fullname: Wong, Chi‐Huey email: chwong@gate.sinica.edu.tw organization: The Scripps Research Institute – sequence: 11 givenname: Cheng‐Chung orcidid: 0000-0002-2562-0658 surname: Wang fullname: Wang, Cheng‐Chung email: wangcc@chem.sinica.edu.tw organization: Academia Sinica |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33634934$$D View this record in MEDLINE/PubMed |
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| Keywords | carbohydrates hydroxyl glycosylation diastereoselectivity predictive algorithms |
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| SSID | ssj0028806 |
| Score | 2.5752246 |
| Snippet | The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants... |
| SourceID | proquest pubmed crossref wiley |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 12413 |
| SubjectTerms | Algorithms Automation Carbohydrates Computer applications diastereoselectivity Donors (electronic) Glycosylation hydroxyl Hydroxyl groups predictive algorithms Reactivity Software Stereoselectivity |
| Title | Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202013909 https://www.ncbi.nlm.nih.gov/pubmed/33634934 https://www.proquest.com/docview/2528071238 https://www.proquest.com/docview/2494301207 |
| Volume | 60 |
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