Search engine for discovering works of Art, research articles, and books related to Art and Culture
Javascript must be enabled to continue!
Taming Unhindered Alkyl Azides by Intramolecular Hydrogen-Azide Interaction for Discriminative Conjugation onto Alkyl Diazides
View through CrossRef
We report herein the unique reactivities of α-azido secondary acetamides (α-AzSAs) as minimal and unhindered azide structures. The NH–azide interaction in the α-AzSAs, supposed by DFT calculation, allowed selective conjugation in the presence of other azido moieties. With Staudinger-Bertozzi ligation, α-AzSAs proceeded the conjugation prior to the other primary alkyl azides. On the other hand, in propargyl cation-mediated triazole synthesis, other alkyl azides, including tertiary alkyl azides, underwent the conjugation faster than α-AzSAs. We also demonstrated discriminative integration of the functional components onto the diazide modular hubs.
American Chemical Society (ACS)
Title: Taming Unhindered Alkyl Azides by Intramolecular Hydrogen-Azide Interaction for Discriminative Conjugation onto Alkyl Diazides
Description:
We report herein the unique reactivities of α-azido secondary acetamides (α-AzSAs) as minimal and unhindered azide structures.
The NH–azide interaction in the α-AzSAs, supposed by DFT calculation, allowed selective conjugation in the presence of other azido moieties.
With Staudinger-Bertozzi ligation, α-AzSAs proceeded the conjugation prior to the other primary alkyl azides.
On the other hand, in propargyl cation-mediated triazole synthesis, other alkyl azides, including tertiary alkyl azides, underwent the conjugation faster than α-AzSAs.
We also demonstrated discriminative integration of the functional components onto the diazide modular hubs.
Related Results
Insight on the Factors Controlling the Equilibrium of Allylic Azides
Insight on the Factors Controlling the Equilibrium of Allylic Azides
Several
allylic azides with different double bond substitution were studied to
understand the factors governing their equilibrium using density functional
theory along with quan...
New Combinations of Organic Azides and Adjacent Functional Groups
New Combinations of Organic Azides and Adjacent Functional Groups
AbstractThe rapid decay of organic azides with loss of dinitrogen is a very exothermic process and is the reason for the explosive properties of these compounds, which have to be h...
Compressibility of Inorganic Azides
Compressibility of Inorganic Azides
The compressibility of α lead azide, β lead azide, barium azide, potassium azide, sodium azide, and thallium azide have been measured by single-crystal x-ray diffraction techniques...
Azides in the Synthesis of Various Heterocycles
Azides in the Synthesis of Various Heterocycles
In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed,...
Abstract 4593: Glycoengineered antibodies for click chemistry applications
Abstract 4593: Glycoengineered antibodies for click chemistry applications
Abstract
Antibody-drug conjugates (ADC) hold considerable promise as anticancer agents. A critical determinant of the effectiveness of ADCs is the chemistry that is ...
Elucidating hydrogen-solid interactions using computational modeling
Elucidating hydrogen-solid interactions using computational modeling
Hydrogen has significant chemical utility, both as a synthetic reagent and as an energy carrier. As the world moves away from fossil fuels being the predominant energy carrier, the...
SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS
SYNTHESIS OF AMINO ACIDS FROM SUBSTITUTED CYANOACETIC ESTERS
Nine α-amino acids, namely, dl-α-aminoundecylic acid, dl-α-aminostearic acid, dl-α-amino-β-methylcaproic acid, dl-α-amino-β-ethylvaleric acid, dl-α-amino-β-methylenanthic acid, dl-...
Effects of Sodium Azide on Platelet Function
Effects of Sodium Azide on Platelet Function
SummarySodium azide in low concentrations (0.1-10 μM) was found to have inhibitory effects on human platelet function. Primary aggregation induced by ADP, epinephrine, thrombin and...