Pyrroloindole-Based Dynamic Combinatorial Chemistry

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Abstract

We report a new class of building blocks for Dynamic Combinatorial Chemistry (DCC) based approach. The new building block (L-PI) is fluorescent (Φ = 48%) and relatively stable towards
on the pyrroloindole scaffold. The attachment of l-cysteine on the α, α′ positions of the core makes thermal and photodegradation. The chirality of the cysteine is transferred to the electron-rich the molecule suitable for disulfide exchange in aqueous dynamic combinatorial libraries (DCLs). pyrroloindole core. Homo- and heterochiral DCLs of L-PI with electron-deficient L- and D- The synthesis of the core follows a modified version of the Knoevenagel–Hemetsberger approach.
naphthalenediimide (NDI) lead to similar library distributions regardless of the enantiomer used.
The new building block (l-PI) is fluorescent (Φ = 48%) and relatively stable towards thermal and When no salt is present, the major component is a dimer, while dimers and tetramers are obtained
photodegradation. The chirality of the cysteine is transferred to the electron-rich pyrroloindole core.
at increased ionic strength.
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 Keywcoomrdpso:ndenytniasma dicimcoemr, wbihnialetodriimalercshaenmditsettrrya;mpeyrrsraorleooinbdtaoinlesd; acthinracrleitays;ediisounlifcidsterength.
Original languageEnglish
Article number726
JournalSymmetry
Volume12
Issue number5
DOIs
Publication statusPublished - 3 May 2020

Keywords

  • dynamic combinatorial chemistry
  • disulfide
  • pyrroloindoles
  • chirality

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