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Stereoselective chemoenzymatic synthesis of the four stereoisomers of l-2-(2-carboxycyclobutyl)glycine and pharmacological characterization at human excitatory amino acid transporter subtypes 1, 2,…
Four stereoisomeric compounds were synthesized in good yield and high enantiomeric excess from the corresponding cis and trans-2-oxalylcyclobutanecarboxylic acids 5 and 6 and evaluated as potential ligands for the human excitatory amino acid transporters, subtypes 1, 2, and 3 in the FLIPR membrane potential assay.
(2+2) Photocycloadditions with Chiral Uracil Derivatives: Access to All Four Stereoisomers of 2-Aminocyclobutanecarboxylic Acid
Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence…
Identification of ion pairs in solution by IR spectroscopy: crucial contributions of gas phase data and simulations.
This study shows that the stretching modes of carboxylate are sensitive to both solvent-shared and contact ion pair formation, and illustrates the potential of the gas phase spectroscopic approach for the elucidation of supramolecular structures in electrolyte solutions.
Click Chelators for Platinum‐Based Anticancer Drugs
Triazoles from “click chemistry” are convenient ligands for the formation of platinum complexes bearing combined triazole–amine or triazole–carboxylate moieties. Striking differences in the chelation…
A Selective Deprotection Strategy for the Construction of trans-2-Aminocyclopropanecarboxylic Acid Derived Peptides.
A procedure allowing access to unprecedented tripeptides containing a trans-2-aminocyclopropanecarboxylic acid residue in their central position has been established with full N-Boc protection of all amide groups until the final step.
Chemistry of 4‐Hydroxy‐2‐cyclopentenone Derivatives
The 4-hydroxy-2-cyclopentenone moiety is a highly valued molecular scaffold; it is bestowed with a wide-ranging chemical reactivity profile which synthetic chemists have exploited increasingly over…
Preparation of Cyclobutene Acetals and Tricyclic Oxetanes through Photochemical Tandem and Cascade Reactions.
Small libraries of each compound class were prepared, thus suggesting that this photochemistry approach opens new opportunities for synthesis design and for widening molecular diversity.
12-Helix folding of cyclobutane beta-amino acid oligomers.
Observations suggest a marked preference for the folding of trans-2-aminocyclobutane carboxylic acid oligomers into a well-defined 12-helical conformation in both solution and the solid state.
N-aminoazetidinecarboxylic acid: direct access to a small-ring hydrazino acid.
A short and efficient synthesis of the previously unknown N-aminoazetidinecarboxylic acid has been established using a photochemical [2 + 2] cycloaddition strategy starting from 6-azauracil. Chiral…
Passerini reaction-amine deprotection-acyl migration peptide assembly: efficient formal synthesis of cyclotheonamide C.
- S. Faure, Thomas Hjelmgaard, Stéphane P. Roche, D. Aitken
- Chemistry, BiologyOrganic letters
- 9 February 2009
A short, convergent, formal total synthesis of cyclotheonamide C is described. The key linear pentapeptide intermediate is assembled at the same time as the elaboration of the…