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A thiolactone strategy for straightforward synthesis of disulfide-linked side-chain-to-tail cyclic peptides featuring an N-terminal modification handle

(2018) CHEMBIOCHEM. 19(6). p.641-646
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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

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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 19.6 (2018): 641–646. Print.
APA
Van Lysebetten, D., Felissati, S., Antonatou, E., Carrette, L., Espeel, P., Focquet, E., Du Prez, F., et al. (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.
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): 641–646.
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.
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://dx.doi.org/10.1002/cbic.201700323},
  volume       = {19},
  year         = {2018},
}

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