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. Author manuscript; available in PMC: 2021 Nov 23.
Published in final edited form as: J Am Chem Soc. 2020 Nov 9;142(46):19611–19621. doi: 10.1021/jacs.0c08583

Scheme 2. Enzymatic Extension of 1 to Install Various Outer Core Ganglioside Epitopesa.

Scheme 2.

aReagents and conditions: (a) PmST1, CMP-Neu5Ac, 100 mM Tris-HCl (pH 8.0), 37 °C, 81% for 2, 75% for 5, 74% for 10, 76% for 12; (b) CgtA, UDP-GalNAc, 10 mM MgCl2, 50 mM Tris-HCl (pH 7.5), 37 °C, 92% for 3, 88% for 8; (c) CgtB, UDP-Gal, 10 mM MgCl2, 50 mM Tris-HCl (pH 7.5), 37 °C, 83% for 4, 80% for 9; (d) CstII, CMP-Neu5Ac, 100 mM Tris-HCl (pH 8.0), 37 °C, 76% for 6, 77% for 7, 74% for 13; (e) α2–3,6,8,9 neuraminidase A from Arthrobacter ureafaciens, 5 mM CaCl2, 50 mM sodium acetate (pH 5.5), 37 °C, 94%.