Chlorotrityl Chloride (CTC) Resin as a Reusable Carboxyl Protecting Group

García-Martín, Fayna; Bayó‐Puxán, Núria; Cruz, Luis J.; Bohling, James C.; Alberício, Fernando

doi:10.1002/qsar.200720015

Cited by 35 publications

(35 citation statements)

References 36 publications

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“…These groups graft nucleophiles, such as thiols, [12] amines [13] and carboxylates, [14] allowing cleavage of the final product under mild acidic conditions. In addition, this resin has the advantage that it can be regenerated several times, [15] a fact supported by other studies by our group.…”

Section: Introductionsupporting

confidence: 75%

Effective and Versatile Strategy for the Total Solid‐Phase Synthesis of Alkanethiols for Biological Applications

et al. 2013

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Biological applications increasingly demand tailored surfaces with a range of functional groups. Herein we describe a straightforward and inexpensive method based exclusively on solid‐phase synthesis for the preparation of a variety of customized alkanethiols (ATs). The technique overcomes all the difficulties encountered during the preparation of these molecules in solution. The procedure allows the use of ATs without further purification for the preparation of self‐assembled monolayers on gold, typically used to achieve functional group diversity on this surface.

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Section: Introductionsupporting

confidence: 75%

Effective and Versatile Strategy for the Total Solid‐Phase Synthesis of Alkanethiols for Biological Applications

et al. 2013

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“…In addition, this modular approach should allow efficient access to a broad spectrum of potential acyl donors. For this purpose, the 2‐chlorotrityl chloride (2‐ClTrtCl) resin was considered to be the optimal polymeric support because the anchoring moiety readily reacts with carboxylic acid groups, and the corresponding highly acid‐labile 2‐chlorotrityl esters can be easily cleaved under mildly acidic conditions (see below) . Final esterification at the glutamate side chain required careful optimisation with regard to the selection of the coupling reagents (see Discussion S2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Kinetic Characterisation of Water‐Soluble Fluorogenic Acyl Donors for Transglutaminase 2

et al. 2016

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Small glutamate-containing peptides bearing coumarin derivatives as fluorescent leaving groups attached to the γ-carboxylic acid group of the Glu residue were synthesised and investigated with regard to their potential to act as substrates for transglutaminase 2 (TGase 2). Their synthesis was accomplished by an efficient solid-phase approach. The excellent water solubility of the compounds enabled their extensive kinetic characterisation in the context of TGase 2-catalysed hydrolysis and aminolysis. The influence of the coumarin skeleton's substitution pattern on the kinetic properties was studied. Derivatives containing 7-hydroxy-4-methylcoumarin (HMC) revealed properties superior to those of their 7-hydroxycoumarin counterparts; analogous amides are not accepted as substrates. Z-Glu(HMC)-Gly-OH, which exhibited the best substrate properties out of the investigated derivatives, was selected for representative kinetic characterisation of acyl acceptor substrates and irreversible inhibitors.

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“…1), with the goal of creating fluorophores with varied length Stokes shifts for multicolor imaging applications. Commercially available BODIPY FL was loaded onto chlorotrityl chloride polystyrene resin (CTC-PS) through its carboxylic acid moiety ( 1 ), where the CTC-PS acted as a protecting group for the carboxylic acid 20 . The styryl modification of BODIPY FL was carried out by reacting the core fluorophore with 79 structurally diverse aromatic aldehydes via Knoevenagel condensation ( b ) 16 .…”

Section: Resultsmentioning

confidence: 99%

Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy

Bittel

Davis

Wang

et al. 2018

Sci Rep

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Multicolor microscopy tools necessary to localize and visualize the complexity of subcellular systems are limited by current fluorophore technology. While commercial fluorophores cover spectral space from the ultraviolet to the near infrared region and are optimized for conventional bandpass based fluorescence microscopy, they are not ideal for highly multiplexed fluorescence microscopy as they tend to have short Stokes shifts, restricting the number of fluorophores that can be detected in a single sample to four to five. Herein, we synthesized a library of 95 novel boron-dipyrromethene (BODIPY)-based fluorophores and screened their photophysical, optical and spectral properties for their utility in multicolor microscopy. A subset of our BODIPY-based fluorophores yielded varied length Stokes shifts probes, which were used to create a five-color image using a single excitation with confocal laser scanning microscopy for the first time. Combining these novel fluorophores with conventional fluorophores could facilitate imaging in up to nine to ten colors using linear unmixing based microscopy approaches.

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Chlorotrityl Chloride (CTC) Resin as a Reusable Carboxyl Protecting Group

Cited by 35 publications

References 36 publications

Effective and Versatile Strategy for the Total Solid‐Phase Synthesis of Alkanethiols for Biological Applications

Effective and Versatile Strategy for the Total Solid‐Phase Synthesis of Alkanethiols for Biological Applications

Synthesis and Kinetic Characterisation of Water‐Soluble Fluorogenic Acyl Donors for Transglutaminase 2

Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy

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