Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Changping Zheng (1) , Teodora Bavaro (2) , Sara Tengattini (2) , Andrea Gualla Mascherpa (3) , Matthieu Sollogoub (1) , Yongmin Zhang (1) , Marco Terreni (2, 1)

1 IPCM - Institut Parisien de Chimie Moléculaire
2 UNIPV - Università degli Studi di Pavia = University of Pavia
3 University of Canterbury [Christchurch]

Highly regioselective deprotection of a series of 2‐amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo‐glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo‐glycoproteins with an N‐acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.

Mots clés: Chemoenzymatic synthesis; Carbohydrates; Biocatalysis; Glycosphingolipids; Neo‐glycoproteins

Domaines: Chimie organique; Chimie thérapeutique

Changping Zheng, Teodora Bavaro, Sara Tengattini, Andrea Gualla Mascherpa, Matthieu Sollogoub, et al.. Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives. European Journal of Organic Chemistry, 2019, 2019 (22), pp.3622-3631. ⟨10.1002/ejoc.201900382⟩. ⟨hal-02180805⟩