A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle
- Author
- Dorien Van Lysebetten, Stefania Felissati, Eirini Antonatou (UGent) , Lieselot Carrette (UGent) , Pieter Espeel (UGent) , Evelien Focquet, Filip Du Prez (UGent) and Annemieke Madder (UGent)
- Organization
- Abstract
- The development of straightforward and versatile peptide cyclisation methods is highly desired to meet the demand for more stable peptide-based drugs. Herein, a new method for the synthesis of side-chain-to-tail cyclic peptides with the simultaneous introduction of an N-terminal handle, based on the introduction of an N-terminal thiolactone building block, is described. A primary amine liberates a homocysteine analogue from the thiolactone building block, which further enables cyclisation of the peptide through disulfide-bond formation with a C-terminal cysteamine. Postcyclisation modification can be achieved by using small bifunctional amines. Alternatively, the synthesis of lipopeptides is demonstrated through direct thiolactone opening with long-chain alkyl amines.
- Keywords
- NATIVE CHEMICAL LIGATION, CLICK CHEMISTRY, AMINO-ACIDS, SOLID-PHASE, CYCLIZATION, CHLOROSUCCINIMIDE, CYCLOADDITION, ANTIBIOTICS, DISCOVERY, OLIGOMERS, cyclisation, lactones, peptides, sulfur, synthesis design
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8561218
- MLA
- Van Lysebetten, Dorien, et al. “A Thiolactone Strategy for Straightforward Synthesis of Disulfide-Linked Side-Chain-to-Tail Cyclic Peptides Featuring an N-Terminal Modification Handle.” CHEMBIOCHEM, vol. 19, no. 6, 2018, pp. 641–46, doi:10.1002/cbic.201700323.
- APA
- Van Lysebetten, D., Felissati, S., Antonatou, E., Carrette, L., Espeel, P., Focquet, E., … Madder, A. (2018). A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle. CHEMBIOCHEM, 19(6), 641–646. https://doi.org/10.1002/cbic.201700323
- Chicago author-date
- Van Lysebetten, Dorien, Stefania Felissati, Eirini Antonatou, Lieselot Carrette, Pieter Espeel, Evelien Focquet, Filip Du Prez, and Annemieke Madder. 2018. “A Thiolactone Strategy for Straightforward Synthesis of Disulfide-Linked Side-Chain-to-Tail Cyclic Peptides Featuring an N-Terminal Modification Handle.” CHEMBIOCHEM 19 (6): 641–46. https://doi.org/10.1002/cbic.201700323.
- Chicago author-date (all authors)
- Van Lysebetten, Dorien, Stefania Felissati, Eirini Antonatou, Lieselot Carrette, Pieter Espeel, Evelien Focquet, Filip Du Prez, and Annemieke Madder. 2018. “A Thiolactone Strategy for Straightforward Synthesis of Disulfide-Linked Side-Chain-to-Tail Cyclic Peptides Featuring an N-Terminal Modification Handle.” CHEMBIOCHEM 19 (6): 641–646. doi:10.1002/cbic.201700323.
- Vancouver
- 1.Van Lysebetten D, Felissati S, Antonatou E, Carrette L, Espeel P, Focquet E, et al. A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle. CHEMBIOCHEM. 2018;19(6):641–6.
- IEEE
- [1]D. Van Lysebetten et al., “A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle,” CHEMBIOCHEM, vol. 19, no. 6, pp. 641–646, 2018.
@article{8561218,
abstract = {{The development of straightforward and versatile peptide cyclisation methods is highly desired to meet the demand for more stable peptide-based drugs. Herein, a new method for the synthesis of side-chain-to-tail cyclic peptides with the simultaneous introduction of an N-terminal handle, based on the introduction of an N-terminal thiolactone building block, is described. A primary amine liberates a homocysteine analogue from the thiolactone building block, which further enables cyclisation of the peptide through disulfide-bond formation with a C-terminal cysteamine. Postcyclisation modification can be achieved by using small bifunctional amines. Alternatively, the synthesis of lipopeptides is demonstrated through direct thiolactone opening with long-chain alkyl amines.}},
author = {{Van Lysebetten, Dorien and Felissati, Stefania and Antonatou, Eirini and Carrette, Lieselot and Espeel, Pieter and Focquet, Evelien and Du Prez, Filip and Madder, Annemieke}},
issn = {{1439-4227}},
journal = {{CHEMBIOCHEM}},
keywords = {{NATIVE CHEMICAL LIGATION,CLICK CHEMISTRY,AMINO-ACIDS,SOLID-PHASE,CYCLIZATION,CHLOROSUCCINIMIDE,CYCLOADDITION,ANTIBIOTICS,DISCOVERY,OLIGOMERS,cyclisation,lactones,peptides,sulfur,synthesis design}},
language = {{eng}},
number = {{6}},
pages = {{641--646}},
title = {{A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle}},
url = {{http://doi.org/10.1002/cbic.201700323}},
volume = {{19}},
year = {{2018}},
}
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