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

Abhishek Santra; Yanhong Li; Hai Yu; Teri J. Slack; Peng George Wang; Xi Chen

doi:10.1039/C7CC04090C

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Highly efficient chemoenzymatic synthesis and facile purification of α-Gal pentasaccharyl ceramide Galα3nLc₄βCer†

Abhishek Santra,

^a Yanhong Li,^a Hai Yu,^a Teri J. Slack,^a Peng George Wang^b and Xi Chen

*^a

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* Corresponding authors

^a Department of Chemistry, University of California, One shields Avenue, Davis, CA, USA
E-mail: xiichen@ucdavis.edu
Fax: +1 530 752-8995
Tel: +1 530 754-6037

^b Department of Chemistry and Center of Diagnostics & Therapeutics, Georgia State University, Atlanta, GA 30303, USA

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%.

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Article information

DOI: https://doi.org/10.1039/C7CC04090C
Article type: Communication
Submitted: 27 May 2017
Accepted: 30 Jun 2017
First published: 30 Jun 2017

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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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Chemical Communications