Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the Photolabile Protecting Groups (PPGs)
2.2. Characterization of PPGs
2.2.1. Acid and Alkali Stability of the PPGs
2.2.2. Photolysis of Esterified Compounds (4) and (5)
2.2.3. DKP Side Reactions
2.2.4. Applicability of PPG 4
2.3. Application of PPGs in Cyclic Peptide Synthesis
3. Materials and Methods
3.1. Synthesis of the Photolabile Protecting Groups (PPGs)
General Reduction Procedure
3.2. Photolysis of Esterified Compounds (4) and (5)
3.3. Applicability of PPG 4
3.3.1. General Esterification Procedure
3.3.2. General TFA Deprotection Procedure
3.4. Application of PPGs in Cyclic Peptide Synthesis
3.4.1. General Procedure for Solid-Phase Reactions
3.4.2. Removal of the Npb Group via Photolysis Experiment
3.4.3. Cyclization of Peptides I, II, and III
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | TFA | 20% Piperidine/DMF |
---|---|---|
4a | + a | + |
12a | − b | + |
13a | − | + |
16a | − | + |
17a | − | + |
5a | + | + |
4b 83% | 4ca 72% | 4da 91% | |
4e 80% | 4f 94% | 4g 90% | 4h 93% |
Peptide | Sequences | Observed Mass (Da) [M+H]+ | Theoretical Mass (Da) [M+H]+ |
---|---|---|---|
I | c (SSEDIKE) | 789.361 | 788.836 |
II | c (GPE) TAFLR | 872.496 | 872.134 |
III | c (LRDGE) IILRY | 1228.726 | 1228.693 |
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Chen, T.; Wang, G.; Tang, L.; Yang, H.; Xu, J.; Wen, X.; Sun, Y.; Liu, S.; Peng, T.; Zhang, S.; et al. Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group. Molecules 2022, 27, 2231. https://doi.org/10.3390/molecules27072231
Chen T, Wang G, Tang L, Yang H, Xu J, Wen X, Sun Y, Liu S, Peng T, Zhang S, et al. Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group. Molecules. 2022; 27(7):2231. https://doi.org/10.3390/molecules27072231
Chicago/Turabian StyleChen, Tingting, Gang Wang, Lin Tang, Hongpeng Yang, Jing Xu, Xiaoxue Wen, Yunbo Sun, Shuchen Liu, Tao Peng, Shouguo Zhang, and et al. 2022. "Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group" Molecules 27, no. 7: 2231. https://doi.org/10.3390/molecules27072231