Synthesis of biotinylated bis(D-glucose) derivatives for glucose transporter photoaffinity labelling

Carbohydrate Research
Makoto HashimotoG D Holman

Abstract

New diazirine based bis-glucose derivatives for tagging glucose transporters have been synthesised. These included two biotinylated compounds linked either by an aminocaproate or by a cleavable dithiol link. These compounds have been derivatised via a key skeleton compound that can be easily used for introduction of additional tags. Studies on the erythrocyte glucose transporter (GLUT1) and the insulin-stimulated adipose cell transporter (GLUT4) have revealed the biotinylated photoreactive bis-glucose compounds are effective labelling reagents.

References

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Citations

Nov 10, 2005·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Takenori TomohiroYasumaru Hatanaka
Dec 12, 2001·Bioorganic & Medicinal Chemistry Letters·Makoto HashimotoKensuke Nabeta
Aug 17, 2002·Bioorganic & Medicinal Chemistry Letters·Makoto HashimotoKensuke Nabeta
Apr 18, 2003·Bioorganic & Medicinal Chemistry Letters·Makoto HashimotoKentaro Murakami
Dec 15, 2012·Journal of Carbohydrate Chemistry·Seok-Ho YuJennifer J Kohler
Nov 8, 2005·Chemical & Pharmaceutical Bulletin·Makoto Hashimoto, Yasumaru Hatanaka
Jul 10, 2003·Biochemical and Biophysical Research Communications·Lubna Al-KhaliliAnna Krook
Apr 28, 2004·Bioorganic & Medicinal Chemistry Letters·Makoto HashimotoYasumaru Hatanaka
Jul 22, 2004·American Journal of Physiology. Endocrinology and Metabolism·Ji LiLawrence H Young
Jul 12, 2007·Chembiochem : a European Journal of Chemical Biology·Wen-Wei QiuFa-Jun Nan
Nov 22, 2018·The Biochemical Journal·Geoffrey D Holman
Mar 7, 2015·Chemical & Pharmaceutical Bulletin·Yasumaru Hatanaka
Mar 8, 2007·American Journal of Physiology. Endocrinology and Metabolism·Edward J MillerLawrence H Young
May 28, 2015·American Journal of Physiology. Endocrinology and Metabolism·Stefan R HargettSusanna R Keller
Feb 15, 2013·Chemical Biology & Drug Design·Wenlin HuangLihe Zhang
Jun 22, 2017·Chembiochem : a European Journal of Chemical Biology·Marina Tanasova, Joseph R Fedie
Feb 27, 2007·Biochemical and Biophysical Research Communications·William Roach, Markus Plomann

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