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BGL Reagent Converting Hydrophobic Molecules into Hydrophilic Derivatives
No.154(November 2014)
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Branched glycerol (BGL) 1, which was developed by Nemoto et al., can bind to hydrophobic molecules to make them hydrophilic after the deprotection of the acetonides. 1a and 1b (after reduction of N3) react with succinic anhydride and glutaric anhydride, respectively, and the resulting compounds can further bind to amino groups of target compounds. 1b also reacts with terminal alkynes via the Click reaction. Owing to the lack of asymmetric carbons in 1, stereo isomers don’t form after the reaction, thus several applications using 1, such as the modification of water-indissoluble pharmaceuticals or Drug Delivery Systems (DDS), are expected. Hydroxy groups protected by acetonides can be easily deprotected in mild conditions, and the byproducts can be removed without difficulty.
References
- 1)Preparation of a branched oligoglycerol
- a)H. Nemoto, M. Kamiya, Y. Minami, T. Araki, T. Kawamura, Synlett 2007, 2091.
- b)H. Nemoto, M. Kamiya, A. Nakamoto, A. Katagiri, K. Yoshitomi, T. Kawamura, H. Hattori, Chem. Lett. 2010, 39, 856.
- c)H. Nemoto, H. Hattori, Jpn. Kokai Tokkyo Koho 2011 178698, 2011.
- a)H. Nemoto, M. Kamiya, Y. Minami, T. Araki, T. Kawamura, Synlett 2007, 2091.
- 2)An efficient method for the refinement of 1,3-methyleneglycerol via bridged acetal exchange and the synthesis of a symmetrically branched glycerol trimer
- 3)A quantitative investigation of the water-solubilizing properties of branched oligoglycerols
- 4)Improved performance by replacing iminodiacetic residues with glyceryl residues in symmetrically branched oligoglycerols
- 5)Preparation and properties of branched oligoglycerol modifiers for stabilization of liposomes
- 6)Modification of protein with BGL06, a novel branched oligoglycerol derivative
- 7)Polyalcohol compound and pharmaceutical agent
- H. Nemoto, K. Tsuchiya, M. Kamiya, PCT Int. Appl. WO2008093655, 2008.
- 8)Paclitaxel derivative
- H. Nemoto, K. Tsuchiya, A. Katagiri, Jpn. Kokai Tokkyo Koho 2012 116821, 2012.
- 9)Synthesis and evaluation of water-soluble resveratrol and piceatannol via BGLation
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