Synthesis of Clickable Fluorescent Probes

Two fluorophores, 7-(dimethylamino)-coumarin-4-acetic acid (DMACA, prepared according to literature procedures52 , 53 (link)) and 7-nitrobenzofurazan (NBD, Sigma–Aldrich), were functionalized with an alkyne substituent (Scheme 2) so that they could be coupled to the linezolid–azide analogue 9 by click chemistry. DMACA 23 was reacted with propargylamine in the presence of HATU as coupling agent to give DMACA linked alkyne 24. NBD linked alkyne 26 was prepared by a substitution reaction from NBD-Cl (4-chloro-7-nitrobenzofurazan) 25 by an improved method based on that previously reported in the literature.⁵⁴ The use of Cs₂CO₃ in THF for the substitution gave improved yields compared to aqueous NaHCO₃ in MeOH.Scheme 2

Synthesis of alkyne-functionalised fluorophores. Reagents and conditions: (i) propargylamine, HATU, DIPEA, DMF rt; (ii) propargylamine, Cs₂CO₃, THF.

Free full text: Click here

Phetsang W., Blaskovich M.A., Butler M.S., Huang J.X., Zuegg J., Mamidyala S.K., Ramu S., Kavanagh A.M, & Cooper M.A. (2014). An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants. Bioorganic & Medicinal Chemistry, 22(16), 4490-4498.

Publication 2014

4 chloro 7 nitrobenzofurazan Acetic acid Alkyne Azide Coumarin Dipea Linezolid Nahco3 Propargylamine

Corresponding Organization :

Other organizations : University of Queensland

Top 5 similar protocols

Protocol cited in 3 other protocols

Variable analysis

independent variables

Functionalization of 7-(dimethylamino)-coumarin-4-acetic acid (DMACA) and 7-nitrobenzofurazan (NBD) with an alkyne substituent

dependent variables

Successful coupling of the alkyne-functionalized fluorophores to the linezolid-azide analogue 9 by click chemistry

control variables

The use of HATU as a coupling agent for the reaction of DMACA with propargylamine
The use of Cs2CO3 in THF for the substitution reaction to prepare NBD linked alkyne 26, which gave improved yields compared to the previously reported method using aqueous NaHCO3 in MeOH

Annotations

Based on most similar protocols

Etiam vel ipsum. Morbi facilisis vestibulum nisl. Praesent cursus laoreet felis. Integer adipiscing pretium orci. Nulla facilisi. Quisque posuere bibendum purus. Nulla quam mauris, cursus eget, convallis ac, molestie non, enim. Aliquam congue. Quisque sagittis nonummy sapien. Proin molestie sem vitae urna. Maecenas lorem.

As authors may omit details in methods from publication, our AI will look for missing critical information across the 5 most similar protocols.

About PubCompare

Our mission is to provide scientists with the largest repository of trustworthy protocols and intelligent analytical tools, thereby offering them extensive information to design robust protocols aimed at minimizing the risk of failures.

We believe that the most crucial aspect is to grant scientists access to a wide range of reliable sources and new useful tools that surpass human capabilities.

However, we trust in allowing scientists to determine how to construct their own protocols based on this information, as they are the experts in their field.

Ready to get started?

Revolutionizing how scientists
search and build protocols!