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 oc, a' positions of the core makes the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). The synthesis or 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.
Original language | English |
---|---|
Article number | 726 |
Journal | Symmetry |
Volume | 12 |
Issue number | 5 |
DOIs | |
Publication status | Published - 3 May 2020 |
Bibliographical note
Funding Information:Funding: This research was funded by EPSRC-DTP studentships to T.-M.G. and D.-M.R., grant numbers EB-CH1264 and EB-BB1250, respectively.
Publisher Copyright:
© 2020 by the authors.
Keywords
- Chirality
- Disulfide
- Dynamic combinatorial chemistry
- Pyrroloindoles
ASJC Scopus subject areas
- Computer Science (miscellaneous)
- Chemistry (miscellaneous)
- General Mathematics
- Physics and Astronomy (miscellaneous)
Fingerprint
Dive into the research topics of 'Pyrroloindole-Based Dynamic Combinatorial Chemistry'. Together they form a unique fingerprint.Equipment
-
Electrospray Time-of-Flight Mass Spectrometer (Open-Access)
Material and Chemical Characterisation (MC2)Facility/equipment: Equipment
-
Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)
Material and Chemical Characterisation (MC2)Facility/equipment: Equipment