Wang Linker Free of Side Reactions

Castro, Vida; Rodríguez, Hortensia; Alberício, Fernando

doi:10.1021/ol303367s

Cited by 19 publications

(21 citation statements)

References 17 publications

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“…Cleavage of half of the peptidyl-resin (step iv) afforded the parent peptide 3.1-PP4. The other half was coupled with azidoacetic acid (step v) to produce the azide-modified peptide; this was followed by on-resin CuAAC with Pr-MeIm (step vi), applying the conditions previously described by Castro et al [ 16 ]. After cleavage and purification by reverse-phase high performance liquid chromatography (RP-HPLC), the target MeIm-3.1-PP4 conjugate was obtained in high purity ( Figure S4 ), and its structure was confirmed by ESI-IT MS analysis ( Figure S5 ).…”

Section: Resultsmentioning

confidence: 99%

“Clicking” an Ionic Liquid to a Potent Antimicrobial Peptide: On the Route towards Improved Stability

Gomes

Bessa

Correia

et al. 2020

IJMS

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A covalent conjugate between an antibacterial ionic liquid and an antimicrobial peptide was produced via “click” chemistry, and found to retain the parent peptide’s activity against multidrug-resistant clinical isolates of Gram-negative bacteria, and antibiofilm action on a resistant clinical isolate of Klebsiella pneumoniae, while exhibiting much improved stability towards tyrosinase-mediated modifications. This unprecedented communication is a prelude for the promise held by ionic liquids -based approaches as tools to improve the action of bioactive peptides.

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Section: Resultsmentioning

confidence: 99%

“Clicking” an Ionic Liquid to a Potent Antimicrobial Peptide: On the Route towards Improved Stability

Gomes

Bessa

Correia

et al. 2020

IJMS

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“…The standard catalytic system uses copper (II) salts (e.g., copper sulfate pentahydrate or copper acetate) in the presence of a reducing agent, such as sodium ascorbate or metallic copper. This constantly reduces copper (II) to Cu(I) maintaining significantly high levels of the catalytic species (Tron et al 2008, Castro et al 2012).…”

Section: Huisgen's 13-dipolar Cycloadditionmentioning

confidence: 99%

"Click" chemistry as a tool to create novel biomaterials: a short review

Barbosa

Martins

Gomes

2017

UPjeng

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In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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“…Albericio and coworkers have recently developed a new resin for SPPS with a better performance compared with the traditional Wang resin. 31 This is based on the use of a linker with two features: methoxy groups as the only activating groups of the phenyl ring and a copper(I)-catalyzed click chemistry reaction to anchor it to the solid support. 31…”

Section: Linkers For Sppsmentioning

confidence: 99%

“…31 This is based on the use of a linker with two features: methoxy groups as the only activating groups of the phenyl ring and a copper(I)-catalyzed click chemistry reaction to anchor it to the solid support. 31…”

Section: Linkers For Sppsmentioning

confidence: 99%