Journal
CARBOHYDRATE RESEARCH
Volume 472, Issue -, Pages 115-121Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2018.12.004
Keywords
Chemoenzymatic synthesis; Glycosyltransferase; Lewis a; Sialyl Lewis a; Sialic acid; Protecting group-free glycosylation
Funding
- United States National Institutes of Health [U01GM120419, R01AI130684]
- United State National Science Foundation [DBIO-722538]
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An efficient streamlined chemoenzymatic approach has been developed for gram-scale synthesis of Lewis a angtigen (Le(a)beta ProN(3)) and a library of sialyl Lewis a antigens (sLe(a)beta ProN(3)) containing different sialic acid forms. Intially, commercially available inexpensive N-acetylglucosamine (GlcNAc) was converted to its N'-glycosyl p-toluenesulfonohydrazide in one step. Followed by chemical glycosylation, GlcNAc beta ProN(3) was synthesized using this protecting group-free method in high yield (82%). Sequential one-pot multienzyme (OPME) beta 1-3-galactosylation of GlcNAc beta ProN(3) followed by OPME alpha 1-4-fucosylation reactions produced target Le(a)beta ProN(3) in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida alpha 2-3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLe(a)beta ProN(3) containing naturally occurring or non-natural sialic acid forms in preparative scales.
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