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. 2014 May 7;136(23):8450–8458. doi: 10.1021/ja503545r

Scheme 4. Synthesis of N-Glycopeptide Fragments 1: β-hCG(chitobiose)[S1G22] (A) and 2: β-hCG(chitobiose)[Z23–Y37] (B) and Convergent Approach to Bis-Glycosylated N-Glycopeptide Fragment 1.2: β-hCG(chitobiose)2[S1Y37] via a Double Lansbury Aspartylation (C).

Scheme 4

Amino acid residues bearing acid-labile protecting groups shown in deep red, pseudoproline dipeptides shown in orange (underlined), and Acm-protected Cys residues shown in purple. Chitobiose glycan shown in blue and thioester functionalities shown in green. Cocktail B: 88% TFA, 5% H2O, 5% phenol (PhOH), 2% triisopropylsilane (TIPSH).