Endo-β-N-acetylglucosaminidase catalysed glycosylation: tolerance of enzymes to structural variation of the glycosyl amino acid acceptor

Organic & Biomolecular Chemistry
Yusuke TomabechiAntony J Fairbanks

Abstract

Endo-β-N-Acetylglucosaminidases (ENGases) are highly useful biocatalysts that can be used to synthetically access a wide variety of defined homogenous N-linked glycoconjugates in a convergent manner. The synthetic efficiency of a selection of family GH85 ENGases was investigated as the structure of the acceptor substrate was varied. Several different GlcNAc-asparagine acceptors were synthesised, and used in conjunction with penta- and decasaccharide oxazoline donors. Different enzymes showed different tolerances of modification of the GlcNAc acceptor. Whilst none tolerated modification of either the 4- or 6-hydroxyl, both Endo M and Endo D tolerated modification of OH-3. For Endo D the achievable synthetic efficiency was increased by a factor of three by the use a 3-O-benzyl protected acceptor. The presence of a fucose at position-3 was not tolerated by any of the enzymes assayed.

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Citations

Jan 23, 2016·Chemical Reviews·Shin-ichiro ShodaShiro Kobayashi
Apr 9, 2016·Carbohydrate Research·Pragya Priyanka, Antony J Fairbanks
Apr 18, 2019·Chemical Communications : Chem Comm·Mikkel Haarslev Schröder MarqvorsenSander Izaäk van Kasteren
Apr 7, 2018·Beilstein Journal of Organic Chemistry·Jayashree RajputMadhuri Vangala
Jun 3, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anna Canela-XandriRamon Canela-Garayoa
Mar 10, 2018·Beilstein Journal of Organic Chemistry·Antony J Fairbanks

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