Chemical Synthesis of 23 kDa Glycoprotein by Repetitive Segment Condensation:  A Synthesis of MUC2 Basal Motif Carrying Multiple O-GalNAc Moieties

Peptide thioester corresponding to a MUC2 tandem repeat unit, which retains seven GalNAc moieties, was prepared by the Fmoc method followed by the low TfOH treatment to remove benzyl groups at the carbohydrate portions. The glycosylated peptide thioester was then consecutively joined by the activati...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-10, Vol.127 (39), p.13720-13725
Main Authors: Hojo, Hironobu, Matsumoto, Yoshiyuki, Nakahara, Yuko, Ito, Emi, Suzuki, Yusuke, Suzuki, Minoru, Suzuki, Akemi, Nakahara, Yoshiaki
Format: Article
Language:English
Subjects:
Acetylgalactosamine - chemistry
Amino Acid Sequence
Applied sciences
Exact sciences and technology
Glycoproteins - chemistry
Miscellaneous
Models, Molecular
Molecular Sequence Data
Mucin-2
Mucins - chemistry
Physicochemistry of polymers
Spectrometry, Mass, Electrospray Ionization
Synthetic biopolymers
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Summary:Peptide thioester corresponding to a MUC2 tandem repeat unit, which retains seven GalNAc moieties, was prepared by the Fmoc method followed by the low TfOH treatment to remove benzyl groups at the carbohydrate portions. The glycosylated peptide thioester was then consecutively joined by the activation of a thioester group by silver ions to obtain a MUC2 tandem repeat model composed of 141 amino acids with 42 GalNAc moieties.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja053711b