Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose conjugates linked by direct B-O-C bonds.

Liu, Bowen; Novikova, Nina; Simpson, Miriam; Timmer, Mattie SM; Stocker, Bridget L; Soehnel, Tilo; Ware, David; Brothers, Penelope

Lighting up sugars: fluorescent BODIPY-gluco-furanose and -septanose conjugates linked by direct B-O-C bonds.

Liu, Bowen ; Novikova, Nina ; Simpson, Miriam ; Timmer, Mattie SM ; Stocker, Bridget L ; Soehnel, Tilo ; Ware, David ; Brothers, Penelope

Identifier: http://hdl.handle.net/2292/44490

Issue Date: 2016-06

Reference: Organic and Biomolecular Chemistry 14(23):5205-5209 21 Jun 2016

Rights: Copyright: The Royal Society of Chemistry

Rights (URI): https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm
Rights (URI): https://www.rsc.org/journals-books-databases/open-access/green-open-access/

Abstract:

We report the first O-BODIPY-glucose conjugates, in which the sugar is directly attached to the BODIPY boron through covalent B-O-C bonds. The reaction of Cl-BODIPY with glucose in acetonitrile produced the 1 : 1 α-glucofuranose BODIPY (1), 1 : 2 α-glucofuranose BODIPY (2) and 1 : 2 α-glucoseptanose BODIPY (3) esters. Compound 3 is a rare instance of the unnatural septanose form of glucose, and the first example of a septanose borate.

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