One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities.
Chemoenzymatic synthesis, which combines the flexibility of chemical synthesis and the high selectivity of enzymatic synthesis, is a powerful approach to obtain complex carbohydrates. It is a preferred method for synthesizing sialic acid-containing structures, including those with diverse naturally occurring and non-natural sialic acid forms, different sialyl linkages and different glycans that link to the sialic acid. Starting from N-acetylmannosamine, mannose or their chemically or enzymatically modified derivatives, sialic acid aldolase-catalyzed condensation reaction leads to the formation of sialic acids and their derivatives. These compounds are subsequently activated by a CMP-sialic acid synthetase and transferred to a wide range of suitable acceptors by a suitable sialyltransferase for the formation of sialosides containing natural and non-natural functionalities. The three-enzyme coupled synthesis of sialosides can be carried out in one pot without the isolation of intermediates. The time for synthesis is 4-18 h. Purification and characterization of the product can be completed within 2-3 d.
Yu
Hai
H
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, California 95616, USA.
Chokhawala
Harshal A
HA
Huang
Shengshu
S
Chen
Xi
X
D048168:Escherichia coli K12 / Q000201:enzymology; D007652:Oxo-Acid-Lyases / Q000378:metabolism; D016979:Pasteurella multocida / Q000201:enzymology; D010776:Photobacterium / Q000201:enzymology; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D012799:Sialyltransferases / Q000378:metabolism; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
D012794:Sialic Acids; D014312:Trisaccharides; D012799:Sialyltransferases; D007652:Oxo-Acid-Lyases; C018728:N-acetylneuraminate lyase