The antiviral peptide carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine changes the average conformation of phospholipids in membranes. Biochemistry 1993 Nov 16;32(45):12197-202
Date
11/16/1993Pubmed ID
8218297DOI
10.1021/bi00096a032Scopus ID
2-s2.0-0027359226 (requires institutional sign-in at Scopus site) 7 CitationsAbstract
The influence of the antiviral peptide, carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine (ZfFG), on the average conformation of phosphatidylcholine in hydrated bilayers was investigated with multinuclear solid state magnetic resonance (NMR). Phosphatidylcholine was specifically deuterated (separately) in the choline N-methyls, the alpha and beta positions of the choline, the C2 carbon of the acyl chains, and at all the carbons of the acyl chains of the phosphatidylcholine. Phosphatidylcholine was also synthesized with the carbonyl carbons of the ester bonds between the glycerol and the hydrocarbon chains enriched in 13C. 2H NMR of the phosphatidylcholine perdeuterated in the acyl chains showed a loss of intensity from the deuteriums with the largest quadrupole splitting in the presence of ZfFG, while the remainder of the powder pattern was largely unaffected. The phosphatidylcholine specifically deuterated at the C2 carbon (representative of the C-D bonds giving rise to the largest quadrupole splittings) showed the same loss of intensity suggesting changes in the phospholipid conformation and conformational dynamics near the glycerol. Analysis of the powder patterns in the 13C NMR spectrum of phosphatidylcholine labeled with 13C in the carbonyl carbons revealed a significant change in the average orientation of the sn-1 carbonyl due to the presence of the ZfFG and no change in the sn-2 carbonyl orientation. Changes in the headgroup conformation, as detected by 2H NMR of the deuteriums in the alpha and beta methylenes of the choline headgroup and 31P NMR of the phosphate segment, reflected the electrostatic nature of the interaction of the carboxyl of ZfFG with phosphatidylcholine bilayers.(ABSTRACT TRUNCATED AT 250 WORDS)
Author List
Yeagle PL, Dentino AR, Smith FT, Spooner P, Watts AAuthor
Andrew Dentino BS,DDS,PhD Professor & Program Director of Periodontics in the Surgical Sciences department at Marquette UniversityMESH terms used to index this publication - Major topics in bold
1,2-DipalmitoylphosphatidylcholineAntiviral Agents
Hydrogen
Lipid Bilayers
Magnetic Resonance Spectroscopy
Molecular Conformation
Oligopeptides
Phosphatidylcholines
Phosphorus Isotopes