ArticleJournal of the American Chemical Society2012
Enhanced epimerization of glycosylated amino acids during solid-phase peptide synthesis.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Uncovering bacterial pseudaminylation with pan-specific antibody tools.Nature chemical biology · 2026Article
- Impact of Glycoclustering on Stiffening of MUC5AC Peptides Revealed by High-Efficiency Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Effect of Glycosylation on the Enzymatic Degradation of D-Amino Acid-Containing Peptides.Molecules (Basel, Switzerland) · 2025Article
- Rapid building block-economic synthesis of long, multi-Chemical science · 2024Article
- Epimerisation in Peptide Synthesis.Molecules (Basel, Switzerland) · 2023Review
- Synthesis of glycopeptides and glycopeptide conjugates.Organic & biomolecular chemistry · 2022Review
- Selective Recognition of Carbohydrate Antigens by Germline Antibodies Isolated from AID Knockout Mice.Journal of the American Chemical Society · 2022Article
- A Stable Gold Nanoparticle-Based Vaccine for the Targeted Delivery of Tumor-Associated Glycopeptide Antigens.ACS bio & med chem Au · 2021Article
- Combining flavin photocatalysis with parallel synthesis: a general platform to optimize peptides with non-proteinogenic amino acids.Chemical science · 2021Article
- A biocompatible supramolecular hydrogel with multivalent galactose ligands inhibitingRSC advances · 2020Article
- Recent Reports of Solid-Phase Cyclohexapeptide Synthesis and Applications.Molecules (Basel, Switzerland) · 2018Review
- Sequence Diversification by Divergent C-Terminal Elongation of Peptides.The Journal of organic chemistry · 2018Article
- Total chemical synthesis of glycocin F and analogues:Chemical science · 2018Article
- Article
- Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives.ACS omega · 2017Article
- Synthesis of rhamnosylated arginine glycopeptides and determination of the glycosidic linkage in bacterial elongation factor P.Chemical science · 2017Article
- Structural analysis and unique molecular recognition properties of a Bauhinia forficata lectin that inhibits cancer cell growth.The FEBS journal · 2017Article
- Peptide Lipidation - A Synthetic Strategy to Afford Peptide Based Therapeutics.Advances in experimental medicine and biology · 2017Review
- Advances in Fmoc solid-phase peptide synthesis.Journal of peptide science : an official publication of the European Peptide Society · 2016Review
- Chemoenzymatic synthesis of α-dystroglycan core M1 O-mannose glycans.Chemical communications (Cambridge, England) · 2015Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Glycopeptides are extremely useful for basic research and clinical applications, but access to structurally defined glycopeptides is limited by the difficulties in synthesizing this class of compounds. In this study, we demonstrate that many common peptide coupling conditions used to prepare O-linked glycopeptides result in substantial amounts of epimerization at the α position. In fact, epimerization resulted in up to 80% of the non-natural epimer, indicating that it can be the major product in some reactions. Through a series of mechanistic studies, we demonstrate that the enhanced epimerization relative to nonglycosylated amino acids is due to a combination of factors, including a faster rate of epimerization, an energetic preference for the unnatural epimer over the natural epimer, and a slower overall rate of peptide coupling. In addition, we demonstrate that use of 2,4,6-trimethylpyridine (TMP) as the base in peptide couplings produces glycopeptides with high efficiency and low epimerization. The information and improved reaction conditions will facilitate the preparation of glycopeptides as therapeutic compounds and vaccine antigens.
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Registered trials
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.