Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides

Khanh Ha; Iryna Oleksandrivna Lebedyeva; Sadra Hamedzadeh; Zhiliang Li; Ryan Quiñones; Girinath G. Pillai; Byron Williams; Amir Nasajpour; Kristin Martin; Abdullah M. Asiri; Alan R. Katritzky

doi:10.1002/chem.201304262

Tandem deprotection-dimerization-macrocyclization route to C₂ symmetric cyclo-tetrapeptides

Khanh Ha, Iryna Oleksandrivna Lebedyeva, Sadra Hamedzadeh, Zhiliang Li, Ryan Quiñones, Girinath G. Pillai, Byron Williams, Amir Nasajpour, Kristin Martin, Abdullah M. Asiri, Alan R. Katritzky

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo- dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).

Original language	English (US)
Pages (from-to)	4874-4879
Number of pages	6
Journal	Chemistry - A European Journal
Volume	20
Issue number	17
DOIs	https://doi.org/10.1002/chem.201304262
State	Published - Apr 22 2014
Externally published	Yes

Keywords

benzotriazoles
cyclodimerization
lactamization
macrocycles
peptides

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Organic Chemistry

Access to Document

10.1002/chem.201304262

Cite this

Tandem deprotection-dimerization-macrocyclization route to C₂ symmetric cyclo-tetrapeptides. / Ha, Khanh; Lebedyeva, Iryna Oleksandrivna; Hamedzadeh, Sadra; Li, Zhiliang; Quiñones, Ryan; Pillai, Girinath G.; Williams, Byron; Nasajpour, Amir; Martin, Kristin; Asiri, Abdullah M.; Katritzky, Alan R.

In: Chemistry - A European Journal, Vol. 20, No. 17, 22.04.2014, p. 4874-4879.

Research output: Contribution to journal › Article › peer-review

Ha, Khanh ; Lebedyeva, Iryna Oleksandrivna ; Hamedzadeh, Sadra ; Li, Zhiliang ; Quiñones, Ryan ; Pillai, Girinath G. ; Williams, Byron ; Nasajpour, Amir ; Martin, Kristin ; Asiri, Abdullah M. ; Katritzky, Alan R. / Tandem deprotection-dimerization-macrocyclization route to C₂ symmetric cyclo-tetrapeptides. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 17. pp. 4874-4879.

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AU - Li, Zhiliang

AU - Quiñones, Ryan

AU - Pillai, Girinath G.

AU - Williams, Byron

AU - Nasajpour, Amir

AU - Martin, Kristin

AU - Asiri, Abdullah M.

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