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Highly efficient chemoenzymatic synthesis and facile purification of ?-Gal pentasaccharyl ceramide Gal?3nLc4?Cer.

ABSTRACT: A highly efficient chemoenzymatic method for synthesizing glycosphingolipids using ?-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%.

SUBMITTER: Santra A

PROVIDER: S-EPMC5597046 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

Santra Abhishek A Li Yanhong Y Yu Hai H Slack Teri J TJ Wang Peng George PG Chen Xi X

Chemical communications (Cambridge, England) 20170701 59

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 H2</ ...[more]

PMID: 28695219

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