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Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine

A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe-Tyr or a Tyr-Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted Suzuki-Miyaura reaction for the formation of the macrocycle. First, the feasibility of the solid-phase Miyaura borylation of a 3-iodotyrosyltripeptide was established. Then, the Suzuki-Miyaura reaction was applied to the cross-coupling of linear 3-boronotyrosine-containing peptidyl resins with iodobenzene and with halogenated aromatic amino acids. Finally, this methodology was extended to the synthesis of biaryl cyclic peptides through the preparation of a linear peptidyl resin containing both the required boronate and halogenated derivatives, followed by a microwave-assisted Suzuki-Miyaura macrocyclization

This work was supported by grant AGL2009-13255-C02-02/AGR from MICINN

© European Journal of Organic Chemistry, 2012, vol. 31, p. 6204-6211

Wiley-VCH Verlag

Author: Afonso Afonso, Ana
Cussó Forest, Olaf
Feliu Soley, Lídia
Planas i Grabuleda, Marta
Date: 2012 November
Abstract: A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe-Tyr or a Tyr-Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted Suzuki-Miyaura reaction for the formation of the macrocycle. First, the feasibility of the solid-phase Miyaura borylation of a 3-iodotyrosyltripeptide was established. Then, the Suzuki-Miyaura reaction was applied to the cross-coupling of linear 3-boronotyrosine-containing peptidyl resins with iodobenzene and with halogenated aromatic amino acids. Finally, this methodology was extended to the synthesis of biaryl cyclic peptides through the preparation of a linear peptidyl resin containing both the required boronate and halogenated derivatives, followed by a microwave-assisted Suzuki-Miyaura macrocyclization
This work was supported by grant AGL2009-13255-C02-02/AGR from MICINN
Format: application/pdf
ISSN: 1434-193X (versió paper)
1099-0690 (versió electrònica)
Document access: http://hdl.handle.net/10256/12667
Language: eng
Publisher: Wiley-VCH Verlag
Collection: MICINN/PN 2010-2012/ AGL2009-13255-C02-02
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201200832
Articles publicats (D-Q)
Is part of: © European Journal of Organic Chemistry, 2012, vol. 31, p. 6204-6211
Rights: Tots els drets reservats
Subject: Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Reacció de Suzuki-Miyaura
Suzuki-Miyaura reaction
Title: Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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