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Pyrroloindole-based dynamic combinatorial chemistry

DOI: 10.3390/sym12050726 DOI Help

Authors: Tiberiu-marius Gianga (University of Bath; Diamond Light Source) , Dora-maria Răsădean (University of Bath) , G. Dan Pantos (University of Bath)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Symmetry , VOL 12

State: Published (Approved)
Published: May 2020

Open Access Open Access

Abstract: We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based on the pyrroloindole scaffold. The attachment of l-cysteine on the α, α′ positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). The synthesis of the core follows a modified version of the Knoevenagel–Hemetsberger approach. The new building block (l-PI) is fluorescent (Φ = 48%) and relatively stable towards thermal and photodegradation. The chirality of the cysteine is transferred to the electron-rich pyrroloindole core. Homo- and heterochiral DCLs of l-PI with electron-deficient l- and d-naphthalenediimide (NDI) lead to similar library distributions regardless of the enantiomer used. When no salt is present, the major component is a dimer, while dimers and tetramers are obtained at increased ionic strength.

Journal Keywords: dynamic combinatorial chemistry; pyrroloindoles; chirality; disulfide

Subject Areas: Chemistry

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