Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation
Used in solid-phase peptide synthesis (SPPS) for peptides with an acid termination, the 2-chlorotrityl chloride (2-CTC) resin is highly susceptible to moisture, leading to reduced resin loading and lower synthetic yields. It is therefore recommended that the resin be activated with thionyl chloride...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-09-01
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| Series: | Methods and Protocols |
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| Online Access: | https://www.mdpi.com/2409-9279/6/5/82 |
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| author | Tanya Román Gerardo Acosta Beatriz G. de la Torre Constanza Cárdenas Fanny Guzmán Fernando Albericio |
| author_facet | Tanya Román Gerardo Acosta Beatriz G. de la Torre Constanza Cárdenas Fanny Guzmán Fernando Albericio |
| author_sort | Tanya Román |
| collection | DOAJ |
| description | Used in solid-phase peptide synthesis (SPPS) for peptides with an acid termination, the 2-chlorotrityl chloride (2-CTC) resin is highly susceptible to moisture, leading to reduced resin loading and lower synthetic yields. It is therefore recommended that the resin be activated with thionyl chloride (SOCl<sub>2</sub>) before peptide assembly. Here we present an optimized procedure for resin activation that minimizes the use of SOCl<sub>2</sub> as the activation reagent and reduces the activation time. Additionally, we demonstrate the feasibility of reusing the 2-CTC resin when following the activation protocol, achieving comparable results to the first usage of the resin. Moreover, we achieved different degrees of resin activation by varying the amount of SOCl<sub>2</sub>. For instance, the use of 2% SOCl<sub>2</sub> in anhydrous dichloromethane (DCM) allowed up to 44% activation of the resin, thereby making it suitable for the synthesis of longer peptides. Alternatively, employing 25% SOCl<sub>2</sub> in anhydrous DCM resulted in up to 80% activation with a reaction time of only 5 min in both cases. |
| first_indexed | 2024-03-10T21:01:04Z |
| format | Article |
| id | doaj.art-dcc979940a5c48cab72d114a5f1f7d4f |
| institution | Directory Open Access Journal |
| issn | 2409-9279 |
| language | English |
| last_indexed | 2024-03-10T21:01:04Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Methods and Protocols |
| spelling | doaj.art-dcc979940a5c48cab72d114a5f1f7d4f2023-11-19T17:34:54ZengMDPI AGMethods and Protocols2409-92792023-09-01658210.3390/mps6050082Improving 2-Chlorotrityl Chloride (2-CTC) Resin ActivationTanya Román0Gerardo Acosta1Beatriz G. de la Torre2Constanza Cárdenas3Fanny Guzmán4Fernando Albericio5Núcleo Biotecnología Curauma, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, ChileDepartment of Organic Chemistry and CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona, 08028 Barcelona, SpainKwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South AfricaNúcleo Biotecnología Curauma, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, ChileNúcleo Biotecnología Curauma, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, ChileDepartment of Organic Chemistry and CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona, 08028 Barcelona, SpainUsed in solid-phase peptide synthesis (SPPS) for peptides with an acid termination, the 2-chlorotrityl chloride (2-CTC) resin is highly susceptible to moisture, leading to reduced resin loading and lower synthetic yields. It is therefore recommended that the resin be activated with thionyl chloride (SOCl<sub>2</sub>) before peptide assembly. Here we present an optimized procedure for resin activation that minimizes the use of SOCl<sub>2</sub> as the activation reagent and reduces the activation time. Additionally, we demonstrate the feasibility of reusing the 2-CTC resin when following the activation protocol, achieving comparable results to the first usage of the resin. Moreover, we achieved different degrees of resin activation by varying the amount of SOCl<sub>2</sub>. For instance, the use of 2% SOCl<sub>2</sub> in anhydrous dichloromethane (DCM) allowed up to 44% activation of the resin, thereby making it suitable for the synthesis of longer peptides. Alternatively, employing 25% SOCl<sub>2</sub> in anhydrous DCM resulted in up to 80% activation with a reaction time of only 5 min in both cases.https://www.mdpi.com/2409-9279/6/5/822-CTC resin activation2-CTC resin reutilizationresin loadingsolid-phase peptide synthesis |
| spellingShingle | Tanya Román Gerardo Acosta Beatriz G. de la Torre Constanza Cárdenas Fanny Guzmán Fernando Albericio Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation Methods and Protocols 2-CTC resin activation 2-CTC resin reutilization resin loading solid-phase peptide synthesis |
| title | Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation |
| title_full | Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation |
| title_fullStr | Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation |
| title_full_unstemmed | Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation |
| title_short | Improving 2-Chlorotrityl Chloride (2-CTC) Resin Activation |
| title_sort | improving 2 chlorotrityl chloride 2 ctc resin activation |
| topic | 2-CTC resin activation 2-CTC resin reutilization resin loading solid-phase peptide synthesis |
| url | https://www.mdpi.com/2409-9279/6/5/82 |
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