Issue 16, 2024

Chemoselective reaction of methoxyaminomethyl BODIPYs with unprotected carbohydrates: a powerful tool for accessing BODIPY neoglycosides

Abstract

The neoglycosylation of methoxyaminomethyl-appended BODIPYs with unprotected reducing mono-, di-, and trisaccharides produces, in a regio- and stereoselective manner, cyclic N-glycosyl-N-methoxy–BODIPY conjugates, as a relevant class of neoglycosides that display excellent photophysical characteristics in pure water, even at high dye concentrations. In addition, the cellular uptake of some of the neoglycosylated BODIPYs has been confirmed via fluorescence microscopy, and a BODIPY–acarbose conjugate showed comparable enzymatic inhibitory activity to acarbose for two different α-amylases: A. oryzae α-amylase (AOA) and human salivary α-amylase (HSA).

Graphical abstract: Chemoselective reaction of methoxyaminomethyl BODIPYs with unprotected carbohydrates: a powerful tool for accessing BODIPY neoglycosides

Supplementary files

Article information

Article type
Research Article
Submitted
17 May 2024
Accepted
22 Jun 2024
First published
25 Jun 2024
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 4356-4365

Chemoselective reaction of methoxyaminomethyl BODIPYs with unprotected carbohydrates: a powerful tool for accessing BODIPY neoglycosides

A. M. Gómez, L. García-Fernández, A. G. Santana, C. Uriel, L. Gartzia-Rivero, J. Bañuelos, I. Garcia-Moreno, L. Infantes, M. R. Aguilar and J. C. Lopez, Org. Chem. Front., 2024, 11, 4356 DOI: 10.1039/D4QO00886C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements