Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA
1
PolyPeptide, Limhamnsvägen 108, PO Box 30089, 20061 Limhamn, Sweden
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2
PolyPeptide, Bioparc 3, 850 Bd Sebastien Brant, 67400 Illkirch, France
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Publication type: Journal Article
Publication date: 2024-07-29
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
39073347
Abstract
The widely used Fmoc/t-Bu solid-phase peptide synthesis (SPPS) is hampered by relying on corrosive, per/polyfluoroalkyl substance (PFAS) classified trifluoroacetic acid (TFA) as a universal protecting group (PG) removal/resin cleavage reagent. We report that suitable combinations of Brønsted acids (BAs) and Lewis acids (LAs) such as HCl/FeCl3 and AcOH/FeCl3 constitute viable alternatives for TFA as PFAS-free cleavage agents. Using water miscible dimethyl carbonate (DMC) and acetonitrile (MeCN) as solvents enabled diluting cleavage mixtures with suitable aqueous solutions, allowing for direct use in purification in which removal of >99.99% iron from an HCl/FeCl3 induced cleavage was demonstrated.
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Pawlas J. et al. Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA // Organic Letters. 2024. Vol. 26. No. 31. pp. 6787-6791.
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Pawlas J., André C., Rasmussen J. H., Ludemann-Hombourger O. Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA // Organic Letters. 2024. Vol. 26. No. 31. pp. 6787-6791.
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TY - JOUR
DO - 10.1021/acs.orglett.4c02569
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c02569
TI - Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA
T2 - Organic Letters
AU - Pawlas, Jan
AU - André, Christophe
AU - Rasmussen, Jon H
AU - Ludemann-Hombourger, Olivier
PY - 2024
DA - 2024/07/29
PB - American Chemical Society (ACS)
SP - 6787-6791
IS - 31
VL - 26
PMID - 39073347
SN - 1523-7060
SN - 1523-7052
ER -
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BibTex (up to 50 authors)
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@article{2024_Pawlas,
author = {Jan Pawlas and Christophe André and Jon H Rasmussen and Olivier Ludemann-Hombourger},
title = {Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c02569},
number = {31},
pages = {6787--6791},
doi = {10.1021/acs.orglett.4c02569}
}
Cite this
MLA
Copy
Pawlas, Jan, et al. “Brønsted Acid–Lewis Acid (BA–LA) Induced Final Deprotection/Peptide Resin Cleavage in Fmoc/t-Bu Solid-Phase Peptide Synthesis: HCl/FeCl3 and AcOH/FeCl3 as Viable PFAS-Free Alternatives for TFA.” Organic Letters, vol. 26, no. 31, Jul. 2024, pp. 6787-6791. https://pubs.acs.org/doi/10.1021/acs.orglett.4c02569.