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Proximity-induced ligation and one-pot macrocyclization of 1,4-diketone-tagged peptides derived from 2,5-disubstituted furans upon release from the solid support

Alex Manicardi (UGent) , Atiruj Theppawong (UGent) , Marleen Van Troys (UGent) and Annemieke Madder (UGent)
(2023) ORGANIC LETTERS. 25(36). p.6618-6622
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Abstract
1,4-Dione-containing peptides are generated during the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems then react with a-effect nucleophiles, following a Paal-Knorr-like mechanism, for the generation of macrocyclic peptides, occurring after simple resuspension of the crude peptide in water. Conveniently, the in situ generation of the electrophile from a stable furan ring avoids the complications associated with the synthesis of carbonyl-containing peptides. Detailed investigation of the reaction characteristics was first performed on supramolecular coiled-coil systems.
Keywords
CYCLIZATION, BINDING

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Citation

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MLA
Manicardi, Alex, et al. “Proximity-Induced Ligation and One-Pot Macrocyclization of 1,4-Diketone-Tagged Peptides Derived from 2,5-Disubstituted Furans upon Release from the Solid Support.” ORGANIC LETTERS, vol. 25, no. 36, 2023, pp. 6618–22, doi:10.1021/acs.orglett.3c02289.
APA
Manicardi, A., Theppawong, A., Van Troys, M., & Madder, A. (2023). Proximity-induced ligation and one-pot macrocyclization of 1,4-diketone-tagged peptides derived from 2,5-disubstituted furans upon release from the solid support. ORGANIC LETTERS, 25(36), 6618–6622. https://doi.org/10.1021/acs.orglett.3c02289
Chicago author-date
Manicardi, Alex, Atiruj Theppawong, Marleen Van Troys, and Annemieke Madder. 2023. “Proximity-Induced Ligation and One-Pot Macrocyclization of 1,4-Diketone-Tagged Peptides Derived from 2,5-Disubstituted Furans upon Release from the Solid Support.” ORGANIC LETTERS 25 (36): 6618–22. https://doi.org/10.1021/acs.orglett.3c02289.
Chicago author-date (all authors)
Manicardi, Alex, Atiruj Theppawong, Marleen Van Troys, and Annemieke Madder. 2023. “Proximity-Induced Ligation and One-Pot Macrocyclization of 1,4-Diketone-Tagged Peptides Derived from 2,5-Disubstituted Furans upon Release from the Solid Support.” ORGANIC LETTERS 25 (36): 6618–6622. doi:10.1021/acs.orglett.3c02289.
Vancouver
1.
Manicardi A, Theppawong A, Van Troys M, Madder A. Proximity-induced ligation and one-pot macrocyclization of 1,4-diketone-tagged peptides derived from 2,5-disubstituted furans upon release from the solid support. ORGANIC LETTERS. 2023;25(36):6618–22.
IEEE
[1]
A. Manicardi, A. Theppawong, M. Van Troys, and A. Madder, “Proximity-induced ligation and one-pot macrocyclization of 1,4-diketone-tagged peptides derived from 2,5-disubstituted furans upon release from the solid support,” ORGANIC LETTERS, vol. 25, no. 36, pp. 6618–6622, 2023.
@article{01HRET21YM7D8X33RH0FJ1B5DD,
  abstract     = {{1,4-Dione-containing peptides are generated during the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems then react with a-effect nucleophiles, following a Paal-Knorr-like mechanism, for the generation of macrocyclic peptides, occurring after simple resuspension of the crude peptide in water. Conveniently, the in situ generation of the electrophile from a stable furan ring avoids the complications associated with the synthesis of carbonyl-containing peptides. Detailed investigation of the reaction characteristics was first performed on supramolecular coiled-coil systems.}},
  author       = {{Manicardi, Alex and Theppawong, Atiruj and Van Troys, Marleen and Madder, Annemieke}},
  issn         = {{1523-7060}},
  journal      = {{ORGANIC LETTERS}},
  keywords     = {{CYCLIZATION,BINDING}},
  language     = {{eng}},
  number       = {{36}},
  pages        = {{6618--6622}},
  title        = {{Proximity-induced ligation and one-pot macrocyclization of 1,4-diketone-tagged peptides derived from 2,5-disubstituted furans upon release from the solid support}},
  url          = {{http://doi.org/10.1021/acs.orglett.3c02289}},
  volume       = {{25}},
  year         = {{2023}},
}

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