The Reaction of Thio Acids with Azides:  A New Mechanism and New Synthetic Applications

Shangguan, Ning; Katukojvala, Sreenivas; Greenberg, Rachel; Williams, Lawrence J.

doi:10.1021/ja0294919

Cited by 339 publications

(191 citation statements)

References 24 publications

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“…In their work, Manetsch et al utilise the reaction of a thioacid and sulfonyl azide to generate an amide, a reaction that they proposed as particularly suitable for RAS, Figure 20. [97,98] Figure 20 Mechanism for reaction of a sulfonyl azide with a thioacid to generate an amide, termed the 'sulfo-click' reaction.…”

Section: Bcl-x L -Sulfo-click Reactionmentioning

confidence: 99%

Kinetic Template‐Guided Tethering of Fragments

2012

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This thesis is composed of two separate projects: Kinetic Template-Guided Tethering of Fragments and Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1 Degradation after DNA Damage. Kinetic Template-Guided Tethering of FragmentsThe development of a novel methodology for the site-directed discovery of small molecule, protein-binding ligands is described. The protein of interest, with a cysteine thiol (either native or engineered) adjacent to the desired binding pocket, is incubated with mixtures of low molecular weight compounds (fragments) modified with either an acrylamide or a vinyl sulfonamide capture group. Any ligand within the mixture that binds within the pocket brings the capture group into close proximity with the cysteine thiol, promoting a conjugate addition reaction at an increased rate over the background reaction. The capture reaction is designed to be slow, such that during the time course of an experiment, no adduct formation is observed unless the reaction is templated by the protein. By this method, binding ligands are rapidly identified by mass spectrometry analysis of the crude reaction mixtures. The methodology has been termed 'kinetic template-guided tethering'. Design and Synthesis of a Chemical Probe to Dissect the Cellular Signalling Cascade leading to Cyclin D1Degradation after DNA Damage An inhibitor described within the literature was found to attenuate the reduction of cyclin D1 after DNA damage to cells. In order to implement a two-step chemical proteomics strategy to find the molecular target of this inhibitor, a synthesis of the compound with an alkyne appendage was required. The alkyne acts as a functional handle for attachment of a reporter molecule in cells via the Huisgen cycloaddition ('Click') reaction. The design and synthesis of this inhibitor with the alkyne appendage is described.

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Section: Bcl-x L -Sulfo-click Reactionmentioning

confidence: 99%

Kinetic Template‐Guided Tethering of Fragments

2012

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“…B. das metabolische Glycan-Engineering durch den nichtnatürlichen Kohlenhydratstoffwechsel, [166][167][168] die nichtnatürliche Proteintranslation, [169] die Exprimierung über auxotrophe Organismen, [170] die posttranslationale [171a,b] (Schema 23 B). [174] Darüber hinaus wurde eine RuCl 3 -vermittelte Variante mit hohen Ausbeuten für die Umsetzung auch sterisch gehinderter Azide beschrieben. [175] Auf der Grundlage dieser Reaktion wurden außerdem potenzielle chemoselektive Ligationen von Sulfonamidderivaten entwickelt, obgleich die Anwendung zur Ligation längerer Peptide noch aussteht.…”

Section: Spurlose Staudinger-ligationunclassified

Chemoselektive Ligations‐ und Modifikationsstrategien für Peptide und Proteine

2008

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Die Untersuchung biologischer Fragestellungen mit chemischen Methoden wird meist als “Chemische Biologie” bezeichnet und setzt voraus, dass biologisch relevante Makromoleküle, wie Peptide und Proteine, chemisch zugänglich sind. Auf der Festphasensynthese von Peptiden aufbauend wurden viele chemoselektive Ligations‐ und Modifikationstechniken zur Verknüpfung synthetischer Peptide oder funktionaler Einheiten zu größeren synthetischen, biologisch relevanten Makromolekülen entwickelt. Dieser Aufsatz fasst die aktuellen Entwicklungen auf dem Gebiet der chemoselektiven Ligations‐ und Modifikationsstrategien zusammen und illustriert ihre Anwendbarkeit an Beispielen aus der chemischen Totalsynthese von Proteinen bis hin zur Semisynthese natürlicher modifizierter Proteine.

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“…In contrast to carboxylic acids, thioacids have been of considerable interest due to their unique reactivity and selectivity in amide bond formations. Various authors [13][14][15][16][17] have reported elegant methods for N-acylation of amines in peptide synthesis. In 2013, Gopi and co-workers [18] used copper(II) acetate as a catalyst for acylation of amines.…”

Section: Introductionmentioning

confidence: 99%

Mild and eco‐friendly chemoselective acylation of amines in aqueous medium using a green, superparamagnetic, recoverable nanocatalyst

Miraki

Yazdani

Ghandi

et al. 2017

Applied Organom Chemis

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Copper-grafted guanidine acetic acid-modified magnetite nanoparticles (Fe 3 O 4 @GAA-Cu(II)) as a green, superparamagnetic and recoverable nanocatalyst is found to promote quantitative N-acylation of various amines in a very short time with an equimolar amount of thioacetic acid in water at room temperature. This method is found to be highly selective for amines and not sensitive to other functional groups. Mild reaction condition, high selectivity, efficiency, simple workup and excellent yields are some of the major advantages of the procedure.

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The Reaction of Thio Acids with Azides: A New Mechanism and New Synthetic Applications

Cited by 339 publications

References 24 publications

Kinetic Template‐Guided Tethering of Fragments

Kinetic Template‐Guided Tethering of Fragments

Chemoselektive Ligations‐ und Modifikationsstrategien für Peptide und Proteine

Mild and eco‐friendly chemoselective acylation of amines in aqueous medium using a green, superparamagnetic, recoverable nanocatalyst

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