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CC BY 4.0 · SynOpen 2018; 02(03): 0240-0245
DOI: 10.1055/s-0037-1610216
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Separation of the 5- and 6-Carboxy Regioisomers of ROX and JOE Dyes with Examples of N-(3-Azidopropyl)amide Synthesis

Nadezhda S. Baleeva
a   Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russia   Email: baranovmikes@gmail.com
,
Marina B. Zagudaylova
,
Mikhail S. Baranov  *
a   Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russia   Email: baranovmikes@gmail.com
b   Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997, Moscow, Russia
› Author AffiliationsThe authors gratefully acknowledge support from the Russian Foundation for Basic Research, grant 18-03-00094-a. Experiments were in part carried out using the equipment provided by the IBCH сore facility (CKP IBCH, supported by Russian Ministry of Education and Science, grant RFMEFI62117X0018).
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Publication History

Received: 23 May 2018

Accepted after revision: 01 July 2018

Publication Date:
25 July 2018 (online)

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Abstract

Despite the widespread applications of various rhodamine and fluorescein 5- and 6-carboxy derivatives, the preparation of their pure regioisomers, in particular cases, remains a complex task. In the present paper we propose optimized approaches to the synthesis and separation of these isomers of ROX and JOE dyes, and also demonstrate their applicability in the synthesis of the corresponding N-(3-azidopropyl)amides.

Key words

fluorescent dyes - fluorescein - rhodamine - JOE - ROX - click-chemistry - azide

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610216.
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