title: Effective PHIP labeling of bioactive peptides boosts the intensity of the NMR signal.
abstract: A series of novel bioactive derivatives of the sunflower trypsin inhibitor-1 (SFTI-1) suitable for hyperpolarization by parahydrogen-induced polarization (PHIP) was developed. The PHIP activity was achieved by labeling with L-propargylglycine, O-propargyl-L-tyrosine, or 4-pentynoic acid. (1) H NMR signal enhancements (SE) of up to a factor of 70 were achieved in aqueous solution. We found that an isolated spatial location of the triple bond within the respective label and its accessibility for the hydrogenation catalyst are essential factors for the degree of signal enhancement.
authors.affiliation: Eduard-Zintl-Institut für Anorganische und Physikalische Chemie, Technische Universität Darmstadt, Alarich-Weiss-Str. 4, 64287 Darmstadt (Germany) http://www.chemie.tu-darmstadt.de/buntkowsky/
authors.forename: Grit
authors.initials: G
authors.lastname: Sauer
authors.forename: Daichi
authors.initials: D
authors.lastname: Nasu
authors.forename: Daniel
authors.initials: D
authors.lastname: Tietze
authors.forename: Torsten
authors.initials: T
authors.lastname: Gutmann
authors.forename: Simon
authors.initials: S
authors.lastname: Englert
authors.forename: Olga
authors.initials: O
authors.lastname: Avrutina
authors.forename: Harald
authors.initials: H
authors.lastname: Kolmar
authors.forename: Gerd
authors.initials: G
authors.lastname: Buntkowsky
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008958:Models, Molecular; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry*; D011522:Protons; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000480:Alkynes; D005231:Fatty Acids, Unsaturated; D010456:Peptides, Cyclic; D011522:Protons; C448501:SFTI-1 peptide, sunflower; D014443:Tyrosine; C003879:4-pentynoic acid; C009055:propargylglycine; D005998:Glycine
keywords: NMR spectroscopy; PHIP; inhibitors; nuclear spin hyperpolarization; signal enhancement