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One-pot multi-enzyme (OPME) chemoenzymatic synthesis of sialyl-Tn-MUC1 and sialyl-T-MUC1 glycopeptides containing natural or non-natural sialic acid.

Abstract
A series of STn-MUC1 and ST-MUC1 glycopeptides containing naturally occurring and non-natural sialic acids have been chemoenzymatically synthesized from Tn-MUC1 glycopeptide using one-pot multienzyme (OPME) approaches. In situ generation of the sialyltransferase donor cytidine 5'-monophosphate-sialic acid (CMP-Sia) using a CMP-sialic acid synthetase in the presence of an extra amount of cytidine 5'-triphosphate (CTP) and removal of CMP from the reaction mixture by flash C18 cartridge purification allow the complete consumption of Tn-MUC1 glycopeptide for quantitative synthesis of STn-MUC1. A Campylobacter jejuni β1-3GalT (CjCgtBΔ30-His6) mutant has been found to catalyze the transfer of one or more galactose residues to Tn-MUC1 for the synthesis of T-MUC1 and galactosylated T-MUC1. Sialylation of T-MUC1 using Pasteurella multocida α2-3-sialyltransferase 3 (PmST3) with Neisseria meningitidis CMP-sialic acid synthetase (NmCSS) and Escherichia coli sialic acid aldolase in one pot produced ST-MUC1 efficiently. These glycopeptides are potential cancer vaccine candidates.
AuthorsHamed Malekan, Gabriel Fung, Vireak Thon, Zahra Khedri, Hai Yu, Jingyao Qu, Yanhong Li, Li Ding, Kit S Lam, Xi Chen
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 21 Issue 16 Pg. 4778-85 (Aug 15 2013) ISSN: 1464-3391 [Electronic] England
PMID23535562 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
CopyrightCopyright © 2013 Elsevier Ltd. All rights reserved.
Chemical References
  • Antigens, Viral, Tumor
  • Bacterial Proteins
  • Glycopeptides
  • Recombinant Fusion Proteins
  • Sialic Acids
  • sialyl-Tn-MUC1
  • Sialyltransferases
  • N-acetyllactosaminide alpha-2,3-sialyltransferase
  • N-acetylneuraminate synthase
  • Oxo-Acid-Lyases
  • N-acetylneuraminate lyase
Topics
  • Antigens, Viral, Tumor (chemistry)
  • Bacterial Proteins (genetics, metabolism)
  • Base Sequence
  • Campylobacter jejuni (enzymology)
  • Cloning, Molecular
  • Escherichia coli (enzymology)
  • Glycopeptides (biosynthesis, chemistry)
  • Molecular Sequence Data
  • Mutation
  • Neisseria meningitidis (enzymology)
  • Oxo-Acid-Lyases (genetics, metabolism)
  • Pasteurella multocida (enzymology)
  • Recombinant Fusion Proteins (biosynthesis, genetics)
  • Sialic Acids (chemistry)
  • Sialyltransferases (genetics, metabolism)

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