13209-32-0Relevant articles and documents
FlICk (fluorescent isoindole crosslinking) for peptide stapling
Todorovic, Mihajlo,Perrin, David M.
, p. 313 - 332 (2020)
The rigidification of peptide secondary structure via stapling is an important and enduring goal in the development of functional peptides for biochemical and pharmaceutical applications. In addition, the incorporation of fluorophores and chromophores has
Site-Selective Functionalization of (sp3)C?H Bonds Catalyzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor
Gu, Yang,Natoli, Sean N.,Liu, Zhennan,Clark, Douglas S.,Hartwig, John F.
, p. 13954 - 13960 (2019/08/30)
The selective functionalization of one C?H bond over others in nearly identical steric and electronic environments can facilitate the construction of complex molecules. We report site-selective functionalizations of C?H bonds, differentiated solely by rem
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
, p. 224 - 239 (2017/12/08)
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.
