Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine

[Image: see text] Post-translationally modified peptides are important regulating molecules for living organisms. Here, we report the stereoselective total synthesis of β-1,2-linked l-arabinosylated Fmoc-protected hydroxyproline building blocks and their incorporation, together with sulfated tyrosin...

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Autores principales: van de Sande, Jasper W., Albada, Bauke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043930/
https://www.ncbi.nlm.nih.gov/pubmed/36917069
http://dx.doi.org/10.1021/acs.orglett.3c00411
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author van de Sande, Jasper W.
Albada, Bauke
author_facet van de Sande, Jasper W.
Albada, Bauke
author_sort van de Sande, Jasper W.
collection PubMed
description [Image: see text] Post-translationally modified peptides are important regulating molecules for living organisms. Here, we report the stereoselective total synthesis of β-1,2-linked l-arabinosylated Fmoc-protected hydroxyproline building blocks and their incorporation, together with sulfated tyrosine and hydroxyproline, into the plant peptide hormone PSY1. Clean glycopeptides were obtained by performing acetyl removal from the l-arabinose groups prior to deprotection of the neopentyl-protected sulfated tyrosine.
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spelling pubmed-100439302023-03-29 Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine van de Sande, Jasper W. Albada, Bauke Org Lett [Image: see text] Post-translationally modified peptides are important regulating molecules for living organisms. Here, we report the stereoselective total synthesis of β-1,2-linked l-arabinosylated Fmoc-protected hydroxyproline building blocks and their incorporation, together with sulfated tyrosine and hydroxyproline, into the plant peptide hormone PSY1. Clean glycopeptides were obtained by performing acetyl removal from the l-arabinose groups prior to deprotection of the neopentyl-protected sulfated tyrosine. American Chemical Society 2023-03-14 /pmc/articles/PMC10043930/ /pubmed/36917069 http://dx.doi.org/10.1021/acs.orglett.3c00411 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle van de Sande, Jasper W.
Albada, Bauke
Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title_full Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title_fullStr Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title_full_unstemmed Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title_short Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine
title_sort chemical synthesis of glycopeptides containing l-arabinosylated hydroxyproline and sulfated tyrosine
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10043930/
https://www.ncbi.nlm.nih.gov/pubmed/36917069
http://dx.doi.org/10.1021/acs.orglett.3c00411
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