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Peptidomimetics via Iminium Ion Chemistry on Solid Phase: Single, Fused, and Bridged Heterocycles
(Springer Berlin Heidelberg, 2015-12)
Iminium ion chemistry represents a versatile transformation capable of introducing structurally diverse constraints into peptide backbones. The compatibility of iminium ion chemistry with traditional solid-phase peptide ...
Peptidomimetics via Iminium Ion Chemistry on Solid Phase: Single, Fused, and Bridged Heterocycles
(Springer, 2015)
Iminium ion chemistry represents a versatile transformation capable of introducing structurally diverse constraints into peptide backbones. The compatibility of iminium ion chemistry with traditional solid-phase peptide ...
Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization-nucleophilic addition
(Pergamon-Elsevier Science Ltd, 2015-09)
We herein describe the solid-phase synthesis of protected N-oxoalkyl-derivatized peptides designed for subsequent acid-mediated, tandem N-acyliminium ion cyclization-nucleophilic addition reaction. The target compounds ...
Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
(American Chemical Society, 2012-12)
A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective ...
From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
(American Chemical Society, 2014-10)
Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions ...
A joint experimental, in silico and NMR studies towards the rational design of iminium-based organocatalyst derived from renewable sources
(American Chemical Society, 2015-08)
An efficient organocatalyst for iminium-ionbased asymmetric Diels−Alder (DA) reactions has beenrationally designed. The most influential structure−activityrelationships were determined experimentally, while DFTcalculations ...
1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
(American Chemical Society, 2005-08)
(Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted ...
Theoretical insights into the regioselectivity of a Pictet-Spengler reaction: transition state structures leading to salsolinol and isosalsolinol
(Wiley, 2017)
The mechanism of the cyclization step of the Pictet-Spengler reaction between acetaldehyde and dopamine to give salsolinol and isosalsolinol was studied computationally, using density functional theory. The preferential ...
Gas-phase reactions for selective detection of the explosives TNT and RDX
(Royal Soc ChemistryCambridgeInglaterra, 2004)
Mechanistic insight into the acid-catalyzed isomerization of biomass-derived polysubstituted pyrrolidines: an experimental and DFT study
(Royal Society of Chemistry, 2017-01)
The 1,3-dipolar cycloaddition reactions of azomethine ylides is one of the preferred methods for the synthesis of polysubstituted pyrrolidines. The use of chiral dipolarophiles derived from carbohydrates yields enantiomerically ...