FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W1967792315> ?p ?o ?g. }

• W1967792315 endingPage "14387" @default.
• W1967792315 startingPage "14378" @default.
• W1967792315 abstract "Peptoids, or oligomers of N-substituted glycine, are an important class of non-native polymers whose close structural similarity to natural α-peptides and ease of synthesis offer significant advantages for the study of biomolecular interactions and the development of biomimetics. Peptoids that are N-substituted with α-chiral aromatic side chains have been shown to adopt either helical or “threaded loop” conformations, depending upon solvent and oligomer length. Elucidation of the factors that impact peptoid conformation is essential for the development of general rules for the design of peptoids with discrete and novel structures. Here, we report the first study of the effects of pentafluoroaromatic functionality on the conformational profiles of peptoids. This work was enabled by the synthesis of a new, α-chiral amine building block, (S)-1-(pentafluorophenyl)ethylamine (S-2), which was found to be highly compatible with peptoid synthesis (delivering (S)-N-(1-(pentafluorophenyl)ethyl)glycine oligomers). The incorporation of this fluorinated monomer unit allowed us to probe both the potential for π-stacking interactions along the faces of peptoid helices and the role of side chain electrostatics in peptoid folding. A series of homo- and heteropeptoids derived from S-2 and non-fluorinated, α-chiral aromatic amide side chains were synthesized and characterized by circular dichroism (CD) and nuclear magnetic resonance (NMR) spectroscopy. Enhancement of π-stacking by quadrupolar interactions did not appear to play a significant role in stabilizing the conformations of heteropeptoids with alternating fluorinated and non-fluorinated side chains. However, incorporation of (S)-N-(1-(pentafluorophenyl)ethyl)glycine monomers enforced helicity in peptoids that typically exhibit threaded loop conformations. Moreover, we found that the incorporation of a single (S)-N-(1-(pentafluorophenyl)ethyl)glycine monomer could be used to selectively promote looped or helical structure in this important peptoid class by tuning the electronics of nearby heteroatoms. The strategic installation of this monomer unit represents a new approach for the manipulation of canonical peptoid structure and the construction of novel peptoid architectures." @default.
• W1967792315 created "2016-06-24" @default.
• W1967792315 creator A5005939723 @default.
• W1967792315 creator A5072500902 @default.
• W1967792315 date "2006-10-18" @default.
• W1967792315 modified "2023-10-01" @default.
• W1967792315 title "Tuning Peptoid Secondary Structure with Pentafluoroaromatic Functionality: A New Design Paradigm for the Construction of Discretely Folded Peptoid Structures" @default.
• W1967792315 cites W1544965039 @default.
• W1967792315 cites W1964046622 @default.
• W1967792315 cites W1967550539 @default.
• W1967792315 cites W1973981331 @default.
• W1967792315 cites W1977404210 @default.
• W1967792315 cites W1991663757 @default.
• W1967792315 cites W2004507988 @default.
• W1967792315 cites W2008357770 @default.
• W1967792315 cites W2034536462 @default.
• W1967792315 cites W2045642095 @default.
• W1967792315 cites W2048444697 @default.
• W1967792315 cites W2050140989 @default.
• W1967792315 cites W2054808758 @default.
• W1967792315 cites W2058289726 @default.
• W1967792315 cites W2064264445 @default.
• W1967792315 cites W2076980750 @default.
• W1967792315 cites W2083593926 @default.
• W1967792315 cites W2091332750 @default.
• W1967792315 cites W2095049937 @default.
• W1967792315 cites W2096649736 @default.
• W1967792315 cites W2105719066 @default.
• W1967792315 cites W2123650819 @default.
• W1967792315 cites W2149994005 @default.
• W1967792315 cites W2155744992 @default.
• W1967792315 cites W2950839881 @default.
• W1967792315 cites W4246263150 @default.
• W1967792315 doi "https://doi.org/10.1021/ja065248o" @default.
• W1967792315 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17076512" @default.
• W1967792315 hasPublicationYear "2006" @default.
• W1967792315 type Work @default.
• W1967792315 sameAs 1967792315 @default.
• W1967792315 citedByCount "92" @default.
• W1967792315 countsByYear W19677923152012 @default.
• W1967792315 countsByYear W19677923152013 @default.
• W1967792315 countsByYear W19677923152014 @default.
• W1967792315 countsByYear W19677923152015 @default.
• W1967792315 countsByYear W19677923152016 @default.
• W1967792315 countsByYear W19677923152017 @default.
• W1967792315 countsByYear W19677923152018 @default.
• W1967792315 countsByYear W19677923152019 @default.
• W1967792315 countsByYear W19677923152021 @default.
• W1967792315 countsByYear W19677923152022 @default.
• W1967792315 countsByYear W19677923152023 @default.
• W1967792315 crossrefType "journal-article" @default.
• W1967792315 hasAuthorship W1967792315A5005939723 @default.
• W1967792315 hasAuthorship W1967792315A5072500902 @default.
• W1967792315 hasConcept C119599485 @default.
• W1967792315 hasConcept C124790011 @default.
• W1967792315 hasConcept C127413603 @default.
• W1967792315 hasConcept C133571119 @default.
• W1967792315 hasConcept C166940927 @default.
• W1967792315 hasConcept C178790620 @default.
• W1967792315 hasConcept C185592680 @default.
• W1967792315 hasConcept C204921945 @default.
• W1967792315 hasConcept C21951064 @default.
• W1967792315 hasConcept C2776545253 @default.
• W1967792315 hasConcept C2779281246 @default.
• W1967792315 hasConcept C2780474982 @default.
• W1967792315 hasConcept C2780642029 @default.
• W1967792315 hasConcept C33347731 @default.
• W1967792315 hasConcept C521977710 @default.
• W1967792315 hasConcept C55493867 @default.
• W1967792315 hasConcept C62614982 @default.
• W1967792315 hasConcept C71240020 @default.
• W1967792315 hasConceptScore W1967792315C119599485 @default.
• W1967792315 hasConceptScore W1967792315C124790011 @default.
• W1967792315 hasConceptScore W1967792315C127413603 @default.
• W1967792315 hasConceptScore W1967792315C133571119 @default.
• W1967792315 hasConceptScore W1967792315C166940927 @default.
• W1967792315 hasConceptScore W1967792315C178790620 @default.
• W1967792315 hasConceptScore W1967792315C185592680 @default.
• W1967792315 hasConceptScore W1967792315C204921945 @default.
• W1967792315 hasConceptScore W1967792315C21951064 @default.
• W1967792315 hasConceptScore W1967792315C2776545253 @default.
• W1967792315 hasConceptScore W1967792315C2779281246 @default.
• W1967792315 hasConceptScore W1967792315C2780474982 @default.
• W1967792315 hasConceptScore W1967792315C2780642029 @default.
• W1967792315 hasConceptScore W1967792315C33347731 @default.
• W1967792315 hasConceptScore W1967792315C521977710 @default.
• W1967792315 hasConceptScore W1967792315C55493867 @default.
• W1967792315 hasConceptScore W1967792315C62614982 @default.
• W1967792315 hasConceptScore W1967792315C71240020 @default.
• W1967792315 hasIssue "44" @default.
• W1967792315 hasLocation W19677923151 @default.
• W1967792315 hasLocation W19677923152 @default.
• W1967792315 hasOpenAccess W1967792315 @default.
• W1967792315 hasPrimaryLocation W19677923151 @default.
• W1967792315 hasRelatedWork W1964673383 @default.
• W1967792315 hasRelatedWork W1967792315 @default.
• W1967792315 hasRelatedWork W1985435463 @default.
• W1967792315 hasRelatedWork W1995538240 @default.

• next