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

Jasper W. van de Sande; Bauke Albada

doi:10.1021/acs.orglett.3c00411

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

Jasper W. van de Sande, Bauke Albada^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

4 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1907-1911
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.3c00411
Publication status	Published - 24 Mar 2023

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https://edepot.wur.nl/629588Licence: CC BY

LWV19054 Boosting regeneration (BO-68-001-014)
Juranic, M. (Project Leader)
1/01/20 → 31/12/24
Project: LVVN project

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title = "Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine",

abstract = "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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AU - van de Sande, Jasper W.

AU - Albada, Bauke

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Y1 - 2023/3/24

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.3c00411

DO - 10.1021/acs.orglett.3c00411

M3 - Article

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SN - 1523-7060

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SP - 1907

EP - 1911

JO - Organic Letters

JF - Organic Letters

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

Abstract

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LWV19054 Boosting regeneration (BO-68-001-014)

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