ArticleJournal of the American Chemical Society2009
Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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38 citing papers in PubMed, 96 citations in OpenAlex.
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- Synthesis and Preliminary Anticancer Activity Assessment of N-Glycosides of 2-Amino-1,3,4-thiadiazoles.Molecules (Basel, Switzerland) · 2021Article
- Synthesis of structurally-defined polymeric glycosylated phosphoprenols as potential lipopolysaccharide biosynthetic probes.Chemical science · 2021Article
- A facile chemoenzymatic synthesis of SARS-CoV-2 glycopeptides for probing glycosylation functions.Chemical communications (Cambridge, England) · 2021Article
- Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal.Organic & biomolecular chemistry · 2020Article
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- Chemical Synthesis of Human Milk Oligosaccharides: Lacto-The Journal of organic chemistry · 2019Article
- The chemical synthesis of human milk oligosaccharides: Lacto-N-tetraose (Galβ1→3GlcNAcβ1→3Galβ1→4Glc).Carbohydrate research · 2019Article
- The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc).Carbohydrate research · 2019Article
- Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans.The Journal of organic chemistry · 2019Article
- Facile Synthesis of Sugar Lactols via Bromine-Mediated Oxidation of Thioglycosides.Journal of carbohydrate chemistry · 2019Article
- Chemical biology of glycoproteins: From chemical synthesis to biological impact.Methods in enzymology · 2019Article
- Total Chemical Synthesis of Human Thyroid-Stimulating Hormone (hTSH)Tetrahedron · 2018Article
- Designer α1,6-Fucosidase Mutants Enable Direct Core Fucosylation of Intact N-Glycopeptides and N-Glycoproteins.Journal of the American Chemical Society · 2017Article
- Total synthesis of glycosylated proteins.Topics in current chemistry · 2015Review
- Glycotherapy: new advances inspire a reemergence of glycans in medicine.Chemistry & biology · 2014Review
- 'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks.Journal of the American Chemical Society · 2013Article
- Chemical synthesis of highly congested gp120 V1V2 N-glycopeptide antigens for potential HIV-1-directed vaccines.Journal of the American Chemical Society · 2013Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
A highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the beta-domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the beta-subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into beta-hFSH subunit was validated in the context of a model system, providing protected beta-hFSH subunit functionalized with chitobiose at positions 7 and 24.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.