6533b839fe1ef96bd12a58d4

RESEARCH PRODUCT

Fluorescent 3-amino-1,8-naphthalimide Tröger’s bases (3-amino-TBNaps) incorporating protected α-amino acids

Sankarasekaran ShanmugarajuCaroline M. PhelanThorfinnur GunnlaugssonSalvador BlascoSamantha A. Murphy

subject

chemistry.chemical_classificationHydrogen bondStereochemistryOrganic ChemistrySupramolecular chemistryPeptideCrystal structureBiochemistryAmino acidchemistry.chemical_compoundchemistryDrug DiscoveryMoleculeImideDerivative (chemistry)

description

Abstract The synthesis of 3-amino-1,8-naphthalimide Troger’s base’s (TBNaps) 2–4, possessing several amino acids at the imide terminus, from the corresponding 3-amino-1,8-naphthalimide (Naps) units is described. The solid-state X-ray crystal structure of the related 3-amino-TBNaps piperidino-ethyl derivative 1, and its supramolecular packing is also outlined. In these molecules (as demonstrated from the X-ray structure of 1), the two Naps units have an orthogonal arrangement that makes them potentially attractive β-turn mimics for incorporation into peptide and polypeptide structures. The ground and the excited state properties of these systems were evaluated in a range of solvents that varied by polarity and hydrogen bonding ability. This investigation demonstrated that all three compounds possess Internal Charge Transfer (ICT) excited state properties.

yearjournalcountryeditionlanguage
2021-10-01Tetrahedron Letters
https://doi.org/10.1016/j.tetlet.2021.153405