dc.contributor.author
Lin, Mei-Huei
dc.contributor.author
Kuo, Yan-Ting
dc.contributor.author
Le Mai Hoang, Kim
dc.contributor.author
Seeberger, Peter H.
dc.date.accessioned
2025-12-09T06:26:58Z
dc.date.available
2025-12-09T06:26:58Z
dc.identifier.uri
https://refubium.fu-berlin.de/handle/fub188/50722
dc.identifier.uri
http://dx.doi.org/10.17169/refubium-50449
dc.description.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 ( 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.
en
dc.format.extent
9 Seiten
dc.rights
Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
dc.rights.uri
https://creativecommons.org/licenses/by/4.0/
dc.subject
Carbohydrate chemistry
en
dc.subject
Synthetic chemistry methodology
en
dc.subject
human milk oligosaccharides
en
dc.subject.ddc
500 Naturwissenschaften und Mathematik::540 Chemie::540 Chemie und zugeordnete Wissenschaften
dc.title
p-nitrobenzyloxycarbonyl protective group as key to automated glycan assembly of neutral human milk oligosaccharides
dc.type
Wissenschaftlicher Artikel
dc.date.updated
2025-12-09T02:29:15Z
dcterms.bibliographicCitation.articlenumber
10941
dcterms.bibliographicCitation.doi
10.1038/s41467-025-66557-3
dcterms.bibliographicCitation.journaltitle
Nature Communications
dcterms.bibliographicCitation.number
1
dcterms.bibliographicCitation.volume
16
dcterms.bibliographicCitation.url
https://doi.org/10.1038/s41467-025-66557-3
refubium.affiliation
Biologie, Chemie, Pharmazie
refubium.affiliation.other
Institut für Pharmazie
refubium.resourceType.isindependentpub
no
dcterms.accessRights.openaire
open access
dcterms.isPartOf.eissn
2041-1723
refubium.resourceType.provider
DeepGreen
