Diastereoselective Synthesis of Glycosyl Phosphates by Using a Phosphorylase-Phosphatase Combination Catalyst

Patricia Wildberger, Martin Pfeiffer, Lothar Brecker, Bernd Nidetzky

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Sugar phosphates play an important role in metabolism and signaling, but also as constituents of macromolecular structures. Selective phosphorylation of sugars is chemically difficult, particularly at the anomeric center. We report phosphatase-catalyzed diastereoselective "anomeric" phosphorylation of various aldose substrates with α-D-glucose 1-phosphate, derived from phosphorylase-catalyzed conversion of sucrose and inorganic phosphate, as the phosphoryl donor. Simultaneous and sequential two-step transformations by the phosphorylase-phosphatase combination catalyst yielded glycosyl phosphates of defined anomeric configuration in yields of up to 70 % based on the phosphate applied to the reaction. An efficient enzyme-assisted purification of the glycosyl phosphate products from reaction mixtures was established.

LanguageEnglish
Pages15867-15871
Number of pages5
JournalAngewandte Chemie (Weinheim) / International edition in English
Volume54
Issue number52
DOIs
StatusPublished - 21 Dec 2015

Fingerprint

Phosphorylase Phosphatase
Phosphatases
Phosphates
Phosphorylation
Catalysts
Sugar Phosphates
Phosphorylases
Phosphoric Monoester Hydrolases
Metabolism
Sugars
Purification
Sucrose
Sugar (sucrose)
Glucose
Enzymes
Substrates

Keywords

  • biocatalysis
  • phosphatases
  • phosphorylases
  • phosphorylation
  • sugar phosphates

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Diastereoselective Synthesis of Glycosyl Phosphates by Using a Phosphorylase-Phosphatase Combination Catalyst. / Wildberger, Patricia; Pfeiffer, Martin; Brecker, Lothar; Nidetzky, Bernd.

In: Angewandte Chemie (Weinheim) / International edition in English, Vol. 54, No. 52, 21.12.2015, p. 15867-15871.

Research output: Contribution to journalArticleResearchpeer-review

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