Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
Solid‐Phase Synthesis of Biaryl Cyclic Peptides Containing a 3
Biaryl cyclic peptides containing a Phe–Tyr or a Tyr–Tyr linkage have been synthesized by solid-phase Miyaura borylation and microwave-assisted Suzuki–Miyaura macrocyclization. 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
Solid-phase synthesis of biaryl cyclic peptides containing a histidine
A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwave-assisted Suzuki-Miyaura reaction.
[PDF] Solid-phase synthesis of biaryl cyclic peptides containing
The feasibility of the solid-phase intramolecular 4(5)-arylation of a histidine residue to obtain biaryl cyclic peptides bearing a His-Phe linkage was established and it was observed that the Leu-Leu spacer is crucial for the intramolescular arylation.
Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine. Afonso Afonso, Ana. orcId Cussó Forest, Olaf researcherId Cussó Forest, Olaf researcherId Cussó Forest, Olaf
Recent progress of on-resin cyclization for the
Finn''s group described the Wang-resin based peptide head-totail CuAAC cyclization under copper catalyst [] their studies, 11-mer and 19-mer peptide 6 and 7 containing Arg-Gly-Asp (RGD) sequence were synthesized by
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The
Solid-phase synthesis of biaryl cyclic peptides by borylation
DOI: 10.1016/J.TET.2011.01.084 Corpus ID: 94204712; Solid-phase synthesis of biaryl cyclic peptides by borylation and microwave-assisted intramolecular Suzuki–Miyaura reaction
Recent progress of on-resin cyclization for the synthesis of
Cyclopeptidomimetics usually prepared by solid phase peptide synthesis (SPPS) of linear precursors followed by in solution cyclization [1d,3b,4].However, this cyclization step is still considered as a formidable challenge because intermolecular reaction proceeds much faster than intramolecular reaction, thus generating undesired linear oligomers and relevant
Solid-phase synthesis of 5-arylhistidines via a microwave
DOI: 10.1016/J.TET.2008.08.077 Corpus ID: 93527542; Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki–Miyaura cross-coupling @article{Cerezo2008SolidphaseSO, title={Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki–Miyaura cross-coupling}, author={Vanessa Cerezo and Muriel Amblard and Jean Mart{''i}nez and Pascal
Solid-Phase Synthesis of Biaryl Cyclic Peptides
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps.
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
In this context, herein our aim was to extend our expertise in the formation of biaryl linkages to the solid-phase synthesis of biaryl bicyclic peptides. To the best of our knowledge, there is only one example on the preparation of this type of compounds on solid support, even though the final cyclization was performed in solution [24–25]. In
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps.
Solid-phase synthesis of biaryl cyclic peptides containing
A solid -phase strategy for the synthesis of biaryl cyclic peptides containing a sidechain to side chain His-Tyr linkage was developed. The key step was the macrocyclization
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides. A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The
Solid-phase synthesis of biaryl cyclic peptides containing a
A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwave-assisted Suzuki-Miyaura reaction.
Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a
The feasibility of the solid-phase intramolecular 4(5)-arylation of a histidine residue to obtain biaryl cyclic peptides bearing a His-Phe linkage was established and it was observed that the Leu-Leu spacer is crucial for the intramolescular arylation. The feasibility of the solid-phase intramolecular 4(5)-arylation of a histidine residue to obtain biaryl cyclic peptides bearing a His-Phe
Solid-phase synthesis of biaryl cyclic peptides containing
A solid -phase strategy for the synthesis of biaryl cyclic peptides containing a sidechain to side chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwaveassisted Suzuki-Miyaura reaction.
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key
Solid-Phase Synthesis of Biaryl Cyclic Lipopeptides
The solid-phase synthesis of the biaryl cyclic lipopeptides 1−3 was planned according to the retrosynthetic analysis depicted in Scheme 1. Based on our previous experience on the synthesis of biaryl cyclic peptides containing a Phe−Tyr linkage,34 macro-cyclization of the linear peptidyl resin 7 was achieved via a Suzuki−Miyaura cross
Solid-phase synthesis of biaryl cyclic peptides containing a
In summary, we describe the first solid-phase synthesis of biaryl cyclic peptides containing a His-Tyr linkage. The key feature of our synthetic methodology is the cyclization
Solid‐Phase Synthesis of Biaryl Cyclic Peptides
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
Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a 3
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key
Solid-phase synthesis of biaryl cyclic peptides by borylation
Miyaura borylation and Suzuki–Miyaura cross-coupling have been combined to set up an efficient strategy for the solid-phase synthesis of biaryl cyclic peptides.The Miyaura borylation was the key step in obtaining the linear peptidyl resin precursor containing both the boronate and the halogenated derivative of an aromatic amino acid.The Suzuki–Miyaura
Peptide Synthesis
The pioneering work of Bruce Merrifield, which introduced solid phase peptide synthesis (SPPS), dramatically changed the strategy of peptide synthesis and simplified the tedious and demanding steps of purification
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
The formation of biaryl bonds in peptides has been performed through a Suzuki–Miyaura cross-coupling reaction [15 – 19] or via a Pd-catalyzed C–H activation reaction [20 – 21].We have used the former reaction for the solid-phase preparation of biaryl cyclic peptides bearing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr linkage [22 – 23].Our approach involved the synthesis of the linear
Solid-Phase Synthesis of Biaryl Cyclic Lipopeptides Derived
An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe–Tyr, a Tyr–Tyr, or a His–Tyr linkage.
Marta PLANAS | Universitat de Girona, Girona | UDG
A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps.
Solid-phase synthesis of biaryl bicyclic peptides containing a 3
Structure of biaryl bicyclic peptides 1–3.. Results and Discussion Synthesis of the biaryl bicyclic peptide 1. We first planned the synthesis of the biaryl bicyclic peptide 1 incorporating a Phe-Phe linkage based on the retrosynthetic analysis depicted in Scheme 1.According to this analysis, the key steps are the macrolactamization and the intramolecular Suzuki–Miyaura cross coupling.
Solid‐Phase Synthesis of Biaryl Cyclic Peptides Containing a 3‐Aryltyrosine
AbstractA 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
Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a 3
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
Solid-phase synthesis of biaryl cyclic peptides by borylation
Recently, we have described an alternative approach for the preparation of biaryl peptides through solid-phase Miyaura borylation of a phenylalanine residue followed by Suzuki–Miyaura cross-coupling with a range of aryl halides. 6 This approach is advantageous because it avoids the synthesis and purification of the amino acid boronate in solution, and is
Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a 3
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
Solid‐Phase Synthesis of Biaryl Cyclic Peptides
A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe–Tyr or a Tyr–Tyr linkage has been accomplished.
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