- Biochemical characterization of Helicobacter pylori α1–3-fucosyltransferase and its application in the synthesis of fucosylated human milk oligosaccharides
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Fucosylated human milk oligosaccharides (HMOs) have important biological functions. Enzymatic synthesis of such compounds requires robust fucosyltransferases. A C-terminal 66-amino acid truncated version of Helicobacter pylori α1–3-fucosyltransferase (Hp3FT) is a good candidate. Hp3FT was biochemically characterized to identify optimal conditions for enzymatic synthesis of fucosides. While N-acetyllactosamine (LacNAc) and lactose were both suitable acceptors, the former is preferred. At a low guanosine 5′-diphospho-β-L-fucose (GDP-Fuc) to acceptor ratio, Hp3FT selectively fucosylated LacNAc. Based on these enzymatic characteristics, diverse fucosylated HMOs, including 3-fucosyllactose (3-FL), lacto-N-fucopentaose (LNFP) III, lacto-N-neofucopentaose (LNnFP) V, lacto-N-neodifucohexaose (LNnDFH) II, difuco- and trifuco-para-lacto-N-neohexaose (DF-paraLNnH and TF-para-LNnH), were synthesized enzymatically by varying the ratio of the donor and acceptor as well as controlling the order of multiple glycosyltransferase-catalyzed reactions.
- Bai, Jing,Wu, Zhigang,Sugiarto, Go,Gadi, Madhusudhan Reddy,Yu, Hai,Li, Yanhong,Xiao, Cong,Ngo, Alice,Zhao, Baohua,Chen, Xi,Guan, Wanyi
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- Glycosyl Imidates, 65. Efficient Synthesis of the Lewis Antigen X (Lex) Family
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tert-Butyldimethylsilyl 2-azido-4,6-O-benzylideneglucopyranoside 5 proved to be a versatile starting material for the synthesis of the Lex antigen family. 3-O-Fucosylation of 5, ensuing reductive benzylidene ring cleavage, and then 4-O-galactos
- Toepfer, Alexander,Kinzy, Willy,Schmidt, Richard R.
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p. 449 - 464
(2007/10/02)
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- Glycosyl Imidates, 49 - Synthesis of the Octasaccharide Moiety of the Dimeric Lex Antigen
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A versatile synthesis of the basic Galβ(1->4)3)>-GlcNAc trisaccharide building block of the Lex antigen family based on two important findings could be developed.Firstly, selective 3-O-allylation of the readily available azidolactose d
- Bommer, Rene,Kinzy, Willy,Schmidt, Richard R.
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p. 425 - 434
(2007/10/02)
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