Synthesis and Diversification of Macrocyclic Alkynediyl Sulfide Peptides | Zendy

Godin Éric | Zendy; Nguyen Thanh Sacha | Zendy; GuerreroMorales Javier | Zendy; Santandrea Jeffrey | Zendy; Caron Antoine | Zendy; Minozzi Clémentine | Zendy; Beaucage Noémie | Zendy; Rey Bastien | Zendy; Morency Mathieu | Zendy; AbelSnape Xavier | Zendy; Collins Shawn K. | Zendy

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Synthesis and Diversification of Macrocyclic Alkynediyl Sulfide Peptides

Author(s) -

Godin Éric,

Nguyen Thanh Sacha,

GuerreroMorales Javier,

Santandrea Jeffrey,

Caron Antoine,

Minozzi Clémentine,

Beaucage Noémie,

Rey Bastien,

Morency Mathieu,

AbelSnape Xavier,

Collins Shawn K.

Publication year - 2020

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.202003655

Subject(s) - cycloaddition , tripeptide , chemistry , combinatorial chemistry , halide , sulfide , catalysis , peptide synthesis , alkyne , peptide , stereochemistry , organic chemistry , biochemistry

The synthesis of rare macrocyclic alkynediyl sulfides by a Cu‐catalyzed C sp −S cross‐coupling is presented. The catalytic protocol (Cu(MeCN) 4 PF 6 /dtbbpy) promotes macrocyclization of peptides, dipeptides and tripeptides at ambient temperature (14 examples, 23→73 % yields) via thiols and bromoalkynes, and is chemoselective with regards to terminal alkynes. Importantly, the underexplored alkynediyl sulfide functionality incorporates a rigidifying structural element and opens new opportunities for diversification of macrocyclic frameworks through S oxidation, halide addition and azide–alkyne cycloaddition chemistries to integrate sulfones, halides or valuable fluorophores (7 examples, 37→92 % yields).

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