{"doi":"10.1007/s00726-014-1783-2","title":"Impacts of terminal (4R)-fluoroproline and (4S)-fluoroproline residues on polyproline conformation","abstract":null,"journal":"Amino Acids","year":2014,"id":687415,"datarank":0.40620753016533157,"base_score":2.70805020110221,"endowment":2.70805020110221,"self_citation_contribution":0.40620753016533157,"citation_network_contribution":0.0,"self_endowment_contribution":0.40620753016533157,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":14,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1795819,"name":"Jia-Cherng Horng","orcid":null,"position":1,"is_corresponding":false},{"id":1412863,"name":"Yu-Ju Lin","orcid":"0000-0002-6130-4820","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Impacts of terminal (4R)-fluoroproline and (4S)-fluoroproline residues on polyproline conformation","abstract":"Many interests have been focused on prolyl cis-trans isomerization which is related to protein folding and isomer-specific biochemical recognition. Since polyproline can adopt either type I (PPI) helices with all cis amide bonds or type II (PPII) helices with all trans amide bonds, it has been a valuable model to study the prolyl isomerization. Recent studies have shown that stereoelectronic effects govern the stability of PPII structure and the rate of PPII → PPI conversion. To further explore the terminal stereoelectronic effects on polyproline conformation, herein we synthesized a series of host-guest peptides in which (2S,4S)-4-fluoroproline (flp) or (2S,4R)-4-fluoroproline (Flp) residues are incorporated into the C- or N-terminal end of a peptide and studied the thermodynamic and kinetic consequences on polyproline conformation. Circular dichroism measurements revealed that inserting 4-fluoroproline residues into the C terminus of a polyproline peptide induces a great stereoelectronic effect on PPII stability and PPII → PPI conversion rates. From the C terminus, a (Flp)₃ triplet stabilizes PPII structure and increases the transition barrier of PPII → PPI conversion by 1.53 kJ mol⁻¹ while a (flp)₃ triplet destabilizes PPII conformation and reduce the PPII → PPI transition barrier by 4.61 kJ mol⁻¹. In contrast, the 4-fluoroproline substitutions at the N terminus do not exhibit distinct stereoelectronic effects on PPII stability and PPII → PPI conversion rates. Our data demonstrate that the C-terminal stereoelectronic effects have a more dramatic impact on PPII stability and PPII → PPI conversion kinetics.","is_dataset_classified":null,"base_score":2.70805020110221,"endowment":2.70805020110221,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"24947982","pmcid":null,"openalex_id":"https://openalex.org/W2107661093","authors":[],"funders":[],"total_grants":0,"fwci":0.6018,"citation_percentile":0.66351394,"influential_citations":0,"citation_trend":[{"year":2014,"count":1},{"year":2015,"count":2},{"year":2016,"count":1},{"year":2018,"count":2},{"year":2019,"count":1},{"year":2020,"count":1},{"year":2021,"count":3},{"year":2024,"count":2},{"year":2025,"count":1}],"oa_status":"closed","license":"http://www.springer.com/tdm","oa_locations":[{"url":"http://link.springer.com/content/pdf/10.1007/s00726-014-1783-2.pdf","host_type":"publisher"},{"url":"http://link.springer.com/article/10.1007/s00726-014-1783-2/fulltext.html","host_type":"publisher"},{"url":"http://link.springer.com/content/pdf/10.1007/s00726-014-1783-2","host_type":"publisher"},{"url":"https://doi.org/10.1007/s00726-014-1783-2","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/24947982","host_type":"repository"}],"fields_of_study":["biodegradable polymer synthesis and properties","Advanced Polymer Synthesis and Characterization","Chemical Synthesis and Analysis"],"mesh_terms":["Amino Acid Sequence","Circular Dichroism","Fluorine","Kinetics","Models, Molecular","Oligopeptides","Peptides","Proline","Protein Conformation","Stereoisomerism","Thermodynamics","Protein Folding","Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization","Halogenation","Protein Stability"],"keywords":["Polyproline helix","Terminal (telecommunication)","Chemistry","Amino terminal","Stereochemistry","Biochemistry","Peptide sequence","Peptide","Computer science"],"sdg_mappings":[],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-18T21:57:42.288619Z","pmid":null,"pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}