Efficient Method for the Synthesis of an Important Precursor of Constrained Peptides

Brunel, Jean Michel

doi:10.2174/0929866053587093

Cited by 4 publications

(3 citation statements)

References 7 publications

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“…Along similar lines, in 2005, Brunel had extended a similar tactics involving the allylation followed by RCM towards the synthesis of AAA derivative starting with Boc protected glycine derivative 218 (Scheme ) . The cyclic AAA 221 serves as a useful precursor for the synthesis of constrained peptides.…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

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This account covers our work related to the development of various synthetic methodologies since 1994. We summarized our strategies and their application to design various functional molecules. In this regard, we also report the utility of our methodologies in others research work. These methods we report here are simple and efficient for the synthesis of a wide variety of intricate molecules such as heterocycles, polycycles, unusual α‐amino acids, star‐shaped molecules, and modified peptides. For this purpose, we used various transition metal‐based reagents and catalysts. Various popular reactions such as metathesis, Suzuki coupling, [2+2+2] cyclotrimerization were used to assemble these targets. Moreover, rongalite has been used to expand the Diels‐Alder chemistry.

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Section: Metathesis Reactionsmentioning

confidence: 99%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

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“…Further, an AAA derivative of type 5a ″ has been used for the preparation of bicyclic acidic amino acids 11 and 12 , which were later evaluated for anticonvulsant activity (Scheme ) . Brunel reported the synthesis of another derivative of 5a with different protecting groups ( 5a ′) using the above strategy . The synthesis of cyclic amino acid 17 was reported by other workers using different approaches involving alkylation followed by Curtius degradation (Scheme )…”

Section: Cyclic Amino Acid Derivativesmentioning

confidence: 99%

Diversity-Oriented Approaches to Unusual α-Amino Acids and Peptides: Step Economy, Atom Economy, Redox Economy, and Beyond

2013

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Here we describe several useful strategies to a variety of unusual α-amino acid derivatives and peptides based on "building block" approach. These building blocks are suitable for modification at an amino acid as well as at a peptide level. Moreover, these methods have embedded several points for diversification and are capable of producing a library of modified amino acids and peptides. We have employed highly atom-economic processes such as the Diels-Alder reaction, [2 + 2 + 2] cycloaddition, Suzuki-Miyaura cross-coupling, and olefin metathesis as key steps to assemble various unnatural amino acid derivatives and peptides. In some instances, we have used rongalite to generate Diels-Alder precursors.

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“…The reaction was quantitative and performed at room temperature within 30 min. The crude resulting product was hydrolyzed under mild acidic conditions with a solution of citric acid in water to yield the free amine 3 . Compound 3 was treated with (benzyloxy)carbonyl chloride to afford the (benzyloxy)carbonyl (Z) N-protected dialkylated unsaturated amino ester 4 that provided the protected disilylated amino acids 5a – c after hydrosilylation (Scheme ).…”

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confidence: 99%

Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis

et al. 2015

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A concise synthetic pathway yielding to hydrophobic α,α-disubstituted disilylated amino acids based on a hydrosilylation reaction is described. As a first example of utilization in solid-phase peptide synthesis, TESDpg was introduced in replacement of Aib in an alamethicin sequence, leading to analogues with modified physicochemical properties and conserved helical structures. This study highlights the potential of these new amino acids as tools for peptide modulation.

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Efficient Method for the Synthesis of an Important Precursor of Constrained Peptides

Abstract: A practical method for the synthesis of an important precursor of constrained peptides involving only three steps from commercial inexpensive precursors is reported.

Cited by 4 publications

References 7 publications

Development of New Synthetic Strategies, Tactics and their Applications

Development of New Synthetic Strategies, Tactics and their Applications

Diversity-Oriented Approaches to Unusual α-Amino Acids and Peptides: Step Economy, Atom Economy, Redox Economy, and Beyond

Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis

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