Exploring synthetic application of α1,3/4-fucosyltransferase to construct a library of fucosylated glycans

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Exploring synthetic application of α1,3/4-fucosyltransferase to construct a library of fucosylated glycans

Ching-Ching Yu 1 , Teng-Wei Tsai 1 , Jia-Lin Fang 1 , Chin-Yu Liang 1 , Yu-Ting Huang 1 , Jyun-Yi Li 1

1 Department of Chemistry and Biochemistry, National Chung-Cheng University, Min-Hsiung, Taiwan

This work focuses on the synthetic application of L-fucose-containing glycans by Helicobacter pylori α1,3/4-fucosyltransferase (FucTIII). By combining of the sequential one-pot enzymatic system of human milk oligosaccharide (HMOs) production,[1] FucTIII was utilized to synthesize various fucosylated HMOs such as lacto-N-fucopentose V (LNFP V), lacto-N-neofucopentose V (LNnFP V), lacto-N-difucohexaose II (LNDFH II), lacto-N-neodifucohexaose II (LNnDFH II) and LNnDFH III; the other important application of L-fucose-containing glycan synthesis – Lewis antigens such as Lewis X, Lewis Y, Lewis a, Lewis b, sialyl Lewis X, sialyl Lewis a and their derivatives were also achieved. Enzyme kinetics data showed that the catalytic efficiency (kcat/Km) of FucTIII on type II N-acetyl lactosamine (LacNAc) was 50 times higher over the type I LacNAc. Noticeably, the enzyme kinetics revealed that the additional GlcNAc on the non-reducing end of the acceptors would enhance the catalytic efficiency of FucTIII on the glycan acceptors. The availability of structurally defined fucosylated glycans would offer a practical approach for investigating future biological applications.

FucTIII-catalyzed enzymatic synthesis of fucosylated glycans

J.-L. Fang, T.-W. Tsai, C.-Y. Liang, J.-Y. Li, C.-C. Yu, Adv. Synth. Catal. 2018, 360, 3213–3219

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