Direct Carbodiimide-Mediated Conjugation of Carboxylates Using ­Pyridinium<i>p</i>-Toluenesulfonate and Tertiary Amines as Additives

Ficht, Simon; Röglin, Lars; Ziehe, Matthias; Breyer, David; Seitz, Oliver

doi:10.1055/s-2004-834819

Cited by 5 publications

(1 citation statement)

References 7 publications

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“…However, solubility issues could be resolved by adding pyridinium para-toluenesulfonate (PPTS). 38 With the carboxylic ester component in 100-fold excess, HATU was an efficient coupling reagent in DMF/water mixtures. The amide bondforming reactions proceeded smoothly without over acylation.…”

Section: Resultsmentioning

confidence: 99%

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

Homer

Seitz

2023

Synthesis

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Forced intercalation probes (FIT-probes) probes are nucleic acid probes in which an intercalator dye of the thiazole orange (TO) family serves as a surrogate nucleobase. Hybridization of FIT probes is accompanied by enhancements of fluorescence. Looking for ways to increase turn-on and brightness of fluorescence, we herein report the synthesis of new fluorogenic base surrogates. In total, 9 different TO derivatives were introduced into FIT probes. Fluorescence measurements in 6 different sequence revealed that substitution at both the quinoline and the benzothiazole part affects fluorescence turn on upon hybridization and brightness of probe-target duplexes. A TO derivative containing a tricyclic benzothiazole provided FIT probes signaling hybridization by up to 19-fold enhancement of fluorescence. Improved fluorescence quantum yields (Φds up to 0.53) and a high extinction coefficients (ε518 up to 91.000∙M−1∙cm−1) make this dye an interesting, and in some sequences superior alternative to the canonical thiazole orange used previously in FIT probes.

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Section: Resultsmentioning

confidence: 99%

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

Homer

Seitz

2023

Synthesis

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Preparation and characterization of a new derivative of rhodamine B with an alkoxysilane moiety

2008

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An efficient and simple one-pot synthesis of 2-perfluoroalkylated benzo[1,3]dioxole derivatives via double–Michael reaction of fluorinated alkynes

Ndong¹,

Jismy²,

Ngi³

et al. 2018

Journal of Fluorine Chemistry

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Direct Carbodiimide-Mediated Conjugation of Carboxylates Using Pyridiniump-Toluenesulfonate and Tertiary Amines as Additives

Abstract: The use of carboxylates in the carbodiimide-mediated coupling to amines was investigated. The addition of pyridinium ptoluenesulfonate (PPTS) and a tertiary amine was found to significantly improve acylation yields by up to 70%.

Cited by 5 publications

References 7 publications

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

Preparation and characterization of a new derivative of rhodamine B with an alkoxysilane moiety

An efficient and simple one-pot synthesis of 2-perfluoroalkylated benzo[1,3]dioxole derivatives via double–Michael reaction of fluorinated alkynes

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Direct Carbodiimide-Mediated Conjugation of Carboxylates Using ­Pyridiniump-Toluenesulfonate and Tertiary Amines as Additives

Abstract: The use of carboxylates in the carbodiimide-mediated coupling to amines was investigated. The addition of pyridinium ptoluenesulfonate (PPTS) and a tertiary amine was found to significantly improve acylation yields by up to 70%.

Cited by 5 publications

References 7 publications

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

New Thiazole Orange Derivatives for Improved Fluorescence Signaling of DNA FIT Probes

Preparation and characterization of a new derivative of rhodamine B with an alkoxysilane moiety

An efficient and simple one-pot synthesis of 2-perfluoroalkylated benzo[1,3]dioxole derivatives via double–Michael reaction of fluorinated alkynes

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Product

Resources

About

Direct Carbodiimide-Mediated Conjugation of Carboxylates Using Pyridiniump-Toluenesulfonate and Tertiary Amines as Additives