Literature DB >> 27205874

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

Bowen Liu1, Nina Novikova, M Cather Simpson, Mattie S M Timmer, Bridget L Stocker, Tilo Söhnel, David C Ware, Penelope J Brothers.   

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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Year:  2016        PMID： 27205874     DOI： 10.1039/c6ob00726k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  6 in total

1.  Indolyl Septanoside Synthesis for In Vivo Screening of Bacterial Septanoside Hydrolases.

Authors:  Aditya R Pote; Sergi Pascual; Antoni Planas; Mark W Peczuh
Journal:  Int J Mol Sci       Date:  2021-04-26       Impact factor: 5.923

2.  Shedding light on the mitochondrial matrix through a functional membrane transporter.

Authors:  Alberto Blázquez-Moraleja; Ines Sáenz-de-Santa María; María D Chiara; Delia Álvarez-Fernández; Inmaculada García-Moreno; Ruth Prieto-Montero; Virginia Martínez-Martínez; Iñigo López Arbeloa; Jose Luis Chiara
Journal:  Chem Sci       Date:  2019-12-09       Impact factor: 9.825

3.  Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron.

Authors:  Maodie Wang; M Graça H Vicente; Deanna Mason; Petia Bobadova-Parvanova
Journal:  ACS Omega       Date:  2018-05-21

4.  A straightforward synthesis of phenyl boronic acid (PBA) containing BODIPY dyes: new functional and modular fluorescent tools for the tethering of the glycan domain of antibodies.

Authors:  Gina Elena Giacomazzo; Pasquale Palladino; Cristina Gellini; Gianluca Salerno; Veronica Baldoneschi; Alessandro Feis; Simona Scarano; Maria Minunni; Barbara Richichi
Journal:  RSC Adv       Date:  2019-09-30       Impact factor: 4.036

Review 5.  Recent development of boronic acid-based fluorescent sensors.

Authors:  Guiqian Fang; Hao Wang; Zhancun Bian; Jie Sun; Aiqin Liu; Hao Fang; Bo Liu; Qingqiang Yao; Zhongyu Wu
Journal:  RSC Adv       Date:  2018-08-20       Impact factor: 4.036

6.  A Concise Route to Water-Soluble 2,6-Disubstituted BODIPY-Carbohydrate Fluorophores by Direct Ferrier-Type C-Glycosylation.

Authors:  Ana M Gómez; Clara Uriel; Ainhoa Oliden-Sánchez; Jorge Bañuelos; Inmaculada Garcia-Moreno; J Cristobal López
Journal:  J Org Chem       Date:  2021-06-22       Impact factor: 4.354
  6 in total

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