A chemo-biocatalytic approach in the synthesis of β-O-naphtylmethyl-N-peracetylated lactosamine |
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| Institution: | 2. LAQV-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, Caparica, Portugal;1. Department of Chemical Engineering and Analytical Chemistry, Institute for Research on Nutrition and Food Safety (INSA·UB), University of Barcelona, Barcelona, Spain;2. Biochemistry and Molecular Biology Unit, Department of Biology, University of Girona, Girona, Spain;3. Glycobiology in Cancer Group, i3S - Instituto de Investigação e Inovação em Saúde, Ipatimup - Institute of Molecular Pathology and Immunology, University of Porto, Porto, Portugal;4. Biomedical Research Institute of Girona (IdIBGi), Salt, Spain;5. Department of Surgery, Dr. Josep Trueta University Hospital, Girona, Spain;6. Department of Gastroenterology, Dr. Josep Trueta University Hospital, Girona, Spain |
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| Abstract: | A chemo-enzymatic approach combining an enzymatic regioselective hydrolysis of peracetylated N-acetyl-α-d-glucosamine (1) with a mild controlled acyl migration led to 2-acetamido-2-deoxy-1,3,6-tri-O-acetyl-α-d-glucopyranose, which was further used in a glycosylation reaction in the synthesis of β-O-naphtylmethyl-N-peracetylated lactosamine.Candida rugose lipase (CRL) immobilized on octyl-agarose and modified by covering it with polyethyleneimine was the best catalyst in terms of activity, stability and regioselectivity in the hydrolysis of 1, producing the deacetylation in C-6 in 95% overall yield. Other immobilized lipases were not specific or with a very low activity towards the hydrolysis of 1.An acyl chemical migration by incubation of the deacetylated C-6 derivative at pH 8.5, 4 °C, and 10–20% acetonitrile permitted to obtain up to 75% overall yield of the 4-OH derivative product. This molecule was successfully applied in a glycosylation reaction to get the peracetylated α-d-lactosamine and finally, the peracetyl-β-O-naphtylmethyl-lactosamine derivative in 20% overall yield. |
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