ArticlePlant & cell physiology2013
Chemical synthesis of Arabidopsis CLV3 glycopeptide reveals the impact of hydroxyproline arabinosylation on peptide conformation and activity.
Article in Plant & cell physiology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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Who cites it
56 citing papers in PubMed, 126 citations in OpenAlex.
- Plant peptide hormones: three decades of discovery and emerging paradigms.Plant physiology · 2026Review
- Peptide hormones in shaping root system architecture and environmental adaptation: Current advances and translational perspectives.Plant communications · 2026Review
- Developmental robustness of the shoot apical meristem despite sex-chromosome dosage imbalance in Silene latifolia.BMC plant biology · 2026Article
- Regulatory layers of robustness of CLAVATA-WUSCHEL feedback system in stem cell homeostasis.Frontiers in plant science · 2026Review
- Local peptide signalling induces stomatal closure under drought stress.Nature communications · 2025Article
- Tri-arabinosylation facilitates the bioactivity of CLE3 peptide inPlant biotechnology (Tokyo, Japan) · 2025Article
- Peptides and Reactive Oxygen Species Regulate Root Development.International journal of molecular sciences · 2025Review
- Genome-Wide Identification and Functional Analysis ofInternational journal of molecular sciences · 2025Article
- The Small Key to the Treasure Chest: Endogenous Plant Peptides Involved in Symbiotic Interactions.Plants (Basel, Switzerland) · 2025Review
- Peptide hormones in plants.Molecular horticulture · 2025Review
- Macromolecular tool box to elucidate CLAVATA3/EMBRYO SURROUNDING REGION-RELATED-RLK binding, signaling, and downstream effects.Journal of experimental botany · 2024Article
- UncoveringInternational journal of molecular sciences · 2024Article
- Stem Cells: Engines of Plant Growth and Development.International journal of molecular sciences · 2023Review
- The hydroxyproline O-arabinosyltransferase FIN4 is required for tomato pollen intine development.Plant reproduction · 2023Article
- Chemical Synthesis of Glycopeptides containing l-Arabinosylated Hydroxyproline and Sulfated Tyrosine.Organic letters · 2023Article
- The CLAVATA3/ESR-related peptide family in the biofuel crop pennycress.Frontiers in plant science · 2023Article
- Deeper genomic insights into tomato CLE genes repertoire identify new active peptides.BMC genomics · 2022Article
- A SlCLV3-SlWUS module regulates auxin and ethylene homeostasis in low light-induced tomato flower abscission.The Plant cell · 2022Article
- A CLAVATA3-like Gene Acts as a Gynoecium Suppression Function in White Campion.Molecular biology and evolution · 2022Article
- Identification of Diverse Stress-Responsive Xylem Sap Peptides in Soybean.International journal of molecular sciences · 2022Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Arabinosylation of hydroxyproline (Hyp) is a post-translational modification often found in secreted peptide signals in plants. The physiological importance of this modification was highlighted by the finding that CLAVATA3 (CLV3), a key peptide signal for regulating the fate of stem cells in the shoot apical meristem in Arabidopsis, contains three l-arabinose residues linked via linear β-1,2-linkages. However, understanding the functions and properties of arabinosylated peptides has been hindered by difficulties in synthesizing the complex arabinose chain. Here we report the stereoselective total synthesis of β-1,2-linked triarabinosylated CLV3 peptide ([Ara3]CLV3). Chemically synthesized [Ara3]CLV3 restricted stem cell activity more effectively than did unmodified CLV3 peptide. Comparison of mono-, di- and triarabinosylated CLV3 glycopeptides revealed that the biological activity increased progressively as the arabinose chain length increased. Thus, the arabinose chain length of CLV3 is important for its biological activity. Nuclear magnetic resonance spectroscopy and nuclear Overhauser effect-based structure calculations further revealed the structural impact of the arabinose chain on peptide conformation. The arabinose chain of [Ara3]CLV3 extends toward the C-terminal end of the peptide, and its non-reducing end is positioned proximal to the peptide backbone. Consequently, the arabinose chain causes distinct distortion in the C-terminal half of the peptide in a highly directional manner. The established synthetic route of [Ara3]CLV3 will greatly contribute to our understanding of the biology and biochemistry of arabinosylated peptide signals in plants.
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