p-nitrobenzyloxycarbonyl protective group as key to automated glycan assembly of neutral human milk oligosaccharides.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 41350320.
- Also identified by DOI 10.1038/s41467-025-66557-3 and PMC identifier 12686065.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
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 (pNZ) 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 pNZ-protected oligosaccharides underscores the robustness of this approach, while three orthogonal deprotection pathways offer synthetic versatility for HMO compounds.
Medical subject headings
- Milk, Human
- Oligosaccharides
- Polysaccharides