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Peer-reviewedCC BYOrganic letters

Architecture-Guided Sequential Editing of Distinct Disulfides in Unprotected Peptides.

  • Samrat Kundu1
  • Adrija Majumdar1
  • Monika Raj1
  1. 1Department of Chemistry, Emory University, Atlanta, Georgia30322, United States.
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Abstract

Disulfide modification typically relies on global reduction, preventing the selective manipulation of individual disulfide bonds within complex peptides. Here, we show that aromatic, ethyl, and tert-butyl disulfides embedded in fully unprotected peptides exhibit distinct intrinsic reactivities that can be selectively decoded by using matched activation modes. This architecture-guided hierarchy enables sequential chemoselective functionalization without the use of protecting groups. Aromatic disulfides further undergo an orthogonal phosphite-mediated transformation, expanding the repertoire of programmable disulfide editing.

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Cite

BibTeXRIS
BibTeX
@article{kundu2026architectureguided,
  title = {{Architecture-Guided Sequential Editing of Distinct Disulfides in Unprotected Peptides.}},
  author = {Samrat Kundu and Adrija Majumdar and Monika Raj},
  journal = {Organic letters},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.orglett.6c03451},
  url = {https://europepmc.org/article/MED/42912240},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Architecture-Guided Sequential Editing of Distinct Disulfides in Unprotected Peptides.
AU  - Samrat Kundu
AU  - Adrija Majumdar
AU  - Monika Raj
PY  - 2026
DA  - 2026/10/01
JO  - Organic letters
DO  - 10.1021/acs.orglett.6c03451
UR  - https://europepmc.org/article/MED/42912240
AB  - Disulfide modification typically relies on global reduction, preventing the selective manipulation of individual disulfide bonds within complex peptides. Here, we show that aromatic, ethyl, and tert-butyl disulfides embedded in fully unprotected peptides exhibit distinct intrinsic reactivities that can be selectively decoded by using matched activation modes. This architecture-guided hierarchy enables sequential chemoselective functionalization without the use of protecting groups. Aromatic disulfides further undergo an orthogonal phosphite-mediated transformation, expanding the repertoire of programmable disulfide editing.
SN  - 1523-7060
SN  - 1523-7052
ER  -