The Experts below are selected from a list of 465 Experts worldwide ranked by ideXlab platform
Xia Shao - One of the best experts on this subject based on the ideXlab platform.
-
solid supported high throughput organic synthesis of peptide β turn mimetics via tandem Petasis Reaction diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.
-
A practical synthesis of peptide mimetics via the solid-phase Petasis Reaction
Tetrahedron Letters, 2000Co-Authors: Sean R. Klopfenstein, Jack J. Chen, Adam Golebiowski, Sean X. Peng, Xia ShaoAbstract:Abstract The boronic acid Mannich Reaction (Petasis Reaction) is demonstrated on a solid support. Peptide mimetics are formed from N -alkylated amino acid resin esters, glyoxylic acid and boronic acids.
-
Solid supported high-throughput organic synthesis of peptide β-turn mimetics via tandem Petasis Reaction/diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.
Andreas Brunschweiger - One of the best experts on this subject based on the ideXlab platform.
-
translation of the copper bipyridine promoted Petasis Reaction to solid phase coupled dna for encoded library synthesis
Bioorganic & Medicinal Chemistry, 2020Co-Authors: Marco Potowski, Robin Esken, Andreas BrunschweigerAbstract:Abstract The Petasis three-component Reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this Reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis Reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.
-
Translation of the copper/bipyridine-promoted Petasis Reaction to solid phase-coupled DNA for encoded library synthesis.
Bioorganic & medicinal chemistry, 2020Co-Authors: Marco Potowski, Robin Esken, Andreas BrunschweigerAbstract:Abstract The Petasis three-component Reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this Reaction is highly attractive for DNA-encoded small molecule screening library synthesis. The Petasis Reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.
Adam Golebiowski - One of the best experts on this subject based on the ideXlab platform.
-
solid supported high throughput organic synthesis of peptide β turn mimetics via tandem Petasis Reaction diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.
-
A practical synthesis of peptide mimetics via the solid-phase Petasis Reaction
Tetrahedron Letters, 2000Co-Authors: Sean R. Klopfenstein, Jack J. Chen, Adam Golebiowski, Sean X. Peng, Xia ShaoAbstract:Abstract The boronic acid Mannich Reaction (Petasis Reaction) is demonstrated on a solid support. Peptide mimetics are formed from N -alkylated amino acid resin esters, glyoxylic acid and boronic acids.
-
Solid supported high-throughput organic synthesis of peptide β-turn mimetics via tandem Petasis Reaction/diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.
Antonio Guarna - One of the best experts on this subject based on the ideXlab platform.
-
synthesis and conformational analysis of constrained β turn mimetics incorporating a bicyclic turn inducer by use of the Petasis three component Reaction on solid phase
European Journal of Organic Chemistry, 2007Co-Authors: Elisa Danieli, Gloria Menchi, Andrea Trabocchi, Antonio GuarnaAbstract:A new set of β-turn mimetics incorporating a bicyclic turn inducer was achieved by use of the solid-phase Petasis Reaction in a stereoselective fashion. The stereoselectivity of the Reaction turned out to be dependent on the side chain of the amino acid preceding the reverse turn inducer. The β-turn mimetics were stabilized by strong intramolecular 10-membered ring hydrogen bonds, detected by conformational analysis by NMR and molecular modelling, whilst the turn type was controlled by the final amine component. Use of arylboronic acids provided access to chemical diversity at position i + 1, whilst the versatility of the HMBA resin allowed additional diversification to be introduced at the cleavage stage, thus providing a tool for the generation of libraries of β-turn mimetics as privileged structures in combinatorial chemistry.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
-
Synthesis and Conformational Analysis of Constrained β‐Turn Mimetics Incorporating a Bicyclic Turn Inducer by Use of the Petasis Three‐Component Reaction on Solid Phase
European Journal of Organic Chemistry, 2007Co-Authors: Elisa Danieli, Gloria Menchi, Andrea Trabocchi, Antonio GuarnaAbstract:A new set of β-turn mimetics incorporating a bicyclic turn inducer was achieved by use of the solid-phase Petasis Reaction in a stereoselective fashion. The stereoselectivity of the Reaction turned out to be dependent on the side chain of the amino acid preceding the reverse turn inducer. The β-turn mimetics were stabilized by strong intramolecular 10-membered ring hydrogen bonds, detected by conformational analysis by NMR and molecular modelling, whilst the turn type was controlled by the final amine component. Use of arylboronic acids provided access to chemical diversity at position i + 1, whilst the versatility of the HMBA resin allowed additional diversification to be introduced at the cleavage stage, thus providing a tool for the generation of libraries of β-turn mimetics as privileged structures in combinatorial chemistry.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Sean R. Klopfenstein - One of the best experts on this subject based on the ideXlab platform.
-
solid supported high throughput organic synthesis of peptide β turn mimetics via tandem Petasis Reaction diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.
-
A practical synthesis of peptide mimetics via the solid-phase Petasis Reaction
Tetrahedron Letters, 2000Co-Authors: Sean R. Klopfenstein, Jack J. Chen, Adam Golebiowski, Sean X. Peng, Xia ShaoAbstract:Abstract The boronic acid Mannich Reaction (Petasis Reaction) is demonstrated on a solid support. Peptide mimetics are formed from N -alkylated amino acid resin esters, glyoxylic acid and boronic acids.
-
Solid supported high-throughput organic synthesis of peptide β-turn mimetics via tandem Petasis Reaction/diketopiperazine formation
Tetrahedron Letters, 2000Co-Authors: Adam Golebiowski, Sean R. Klopfenstein, Jack J. Chen, Xia ShaoAbstract:Abstract High-throughput organic synthesis of bicyclic diketopiperazines 1 , β-turn mimetics, is described. Starting from Merrifield resin-bound piperazine-2-carboxylic acid, first two (R 4 and R 5 ) side chains are introduced via the Petasis Reaction and subsequent amide bond formation. Unblocking the α-amino group of piperazine-2-carboxylic acid, Boc- N -protected α-amino acid coupling and deprotection followed by cyclative cleavage introduces the remaining R 2 and R 1 side chains.