Human milk oligosaccharides: an enzymatic protection step simplifies the synthesis of 3'- and 6'-O-sialyllactose and their analogues.
We describe a chemo-enzymatic synthesis of 3'- and 6'-O-sialyllactose, two trisaccharides occurring in the 'acidic fraction' of the human milk oligosaccharides and endowed with potential antiadhesive activity. The key step is the highly regioselective 6'-O-acylation of benzyllactoside, which gave access to suitably protected lactose building blocks to be used as acceptors in the sialylation reaction. Moreover, the synthesis of the carboxymethyl and sulfo analogues of the title compounds is reported.
Rencurosi
Anna
A
Department of Organic and Industrial Chemistry, University of Milan, via G. Venezian, I-21-20133 Milan, Italy.
Poletti
Laura
L
Guerrini
Marco
M
Russo
Giovanni
G
Lay
Luigi
L
D000215:Acylation; D002175:Candida / Q000201:enzymology; D002240:Carbohydrate Sequence; D005656:Fungal Proteins / Q000378:metabolism; D006801:Humans; D007785:Lactose / Q000031:analogs & derivatives* / Q000096:biosynthesis* / Q000737:chemistry; D008049:Lipase / Q000378:metabolism; D008895:Milk, Human / Q000201:enzymology*; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry
C421467:3'-sialyllactose; C403777:6'-sialyllactose; D005656:Fungal Proteins; D009844:Oligosaccharides; D008049:Lipase; D007785:Lactose