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Issue 59, 2017
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Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc4βCer

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Abstract

A highly efficient chemoenzymatic method for synthesizing glycosphingolipids using α-Gal pentasaccharyl ceramide as an example is reported here. Enzymatic extension of the chemically synthesized lactosyl sphingosine using efficient sequential one-pot multienzyme (OPME) reactions allowed glycosylation to be carried out in aqueous solutions. Facile C18 cartridge-based quick (<30 minutes) purification protocols were established using minimal amounts of green solvents (CH3CN and H2O). Simple acylation in the last step led to the formation of the target glycosyl ceramide in 4 steps with an overall yield of 57%.

Graphical abstract: Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc4βCer

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Publication details

The article was received on 27 May 2017, accepted on 30 Jun 2017 and first published on 30 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC04090C
Citation: Chem. Commun., 2017,53, 8280-8283
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    Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc4βCer

    A. Santra, Y. Li, H. Yu, T. J. Slack, P. G. Wang and X. Chen, Chem. Commun., 2017, 53, 8280
    DOI: 10.1039/C7CC04090C

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