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This analysis demonstrates enhanced coupling efficiency in chemical synthesis of human milk oligosaccharides, suggesting robustness of the approach.
Human milk oligosaccharides (HMOs) have highly diverse and branched structures that present a significant challenge for chemical synthesis. Here we show that masking the amino group in glucosamine with a p -nitrobenzyloxycarbonyl ( p NZ) protecting group enhances coupling and deprotection efficiency during automated glycan assembly (AGA) of homogeneous HMOs, including the lacto- N -tetraose (LNT), lacto- N -neotetraose (LNnT), lacto- N -fucopentaose (LNFP), lacto- N -difuco-hexaose (LNDFH), and lacto-N-neohexaose (LNnH) series. Deprotection strategies are developed to achieve excellent purity of linear and branched HMO structures. The end-to-end tractability of p NZ-protected oligosaccharides underscores the robustness of this approach, while three orthogonal deprotection pathways offer synthetic versatility for HMO compounds.
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Lin et al. (2025) studied this question.
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