A high-field proton magnetic resonance and nuclear Overhauser effect study of prostaglandin E2

1980 ◽  
Vol 58 (15) ◽  
pp. 1577-1583 ◽  
Author(s):  
George Kotovych ◽  
Gerdy H. M. Aarts ◽  
Glen Bigam
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Nuclear Overhauser Effect ◽  
Double Resonance ◽  
Effect Study ◽  
Prostaglandin E ◽  
Hindered Rotation ◽  
H Nmr ◽  
Proton Resonances ◽  
Nuclear Overhauser

The proton magnetic resonance (1H nmr) spectrum of prostaglandin E2 (PGE2) in CDCl3 at 400 MHz bas been completely analyzed utilizing homonuclear double resonance, inversion recovery, and nOe difference experiments. The nOe difference experiments are used to assign points of configuration, namely the H-10β and the H-10α proton resonances. A spectral analysis shows that the two protons at C-3 and the two protons at C-4 are nonequivalent, indicating a hindered rotation of the chain. This is possibly due to the hairpin conformation of PGE2 in solution.

A nuclear Overhauser effect difference study and a two-dimensional J proton magnetic resonance study of (6S)-prostaglandin I1

1981 ◽  
Vol 59 (10) ◽  
pp. 1449-1454 ◽  
Author(s):  
George Kotovych ◽  
Gerdy H. M. Aarts ◽  
Tom T. Nakashima
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Nuclear Overhauser Effect ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Two Dimensional ◽  
Overhauser Effect ◽  
Effect Difference ◽  
Proton Resonances ◽  
Nuclear Overhauser

High-field nuclear Overhauser effect difference measurements allowed the assignment of the proton resonances for (6S)-prostaglandin I1 in phosphate buffer solutions. The two-dimensional J proton magnetic resonance experiments complemented these studies, as they also allowed the structure of several multiplets to be obtained when these multiplets are hidden by nearby resonances in a normal spectrum. The chemical shifts and coupling constants are compared with the data obtained previously for (6R)-prostaglandin I1.

The solution conformation of prostacyclin as determined by high field proton magnetic resonance techniques

1980 ◽  
Vol 58 (10) ◽  
pp. 974-983 ◽  
Author(s):  
George Kotovych ◽  
Gerdy H. M. Aarts ◽  
Tom T. Nakashima ◽  
Glen Bigam
Keyword(s):  
Magnetic Resonance ◽  
Correlation Time ◽  
Proton Magnetic Resonance ◽  
Double Resonance ◽  
Relaxation Times ◽  
Segmental Motion ◽  
Solution Conformation ◽  
Nmr Spectrum ◽  
H Nmr ◽  
The Difference

The proton magnetic resonance (1H nmr) spectrum at 400 MHz of prostacyclin at pH 10.4 in glycine buffer has been completely analyzed utilizing homonuclear double resonance, inversion recovery, and difference nOe experiments. The spectral analysis shows that the two protons at C-4 are non-equivalent even though they are removed from the asymmetric centres at C-8 and C-9 by five bonds. The difference nOe measurements verify the configuration at C-5.Proton longitudinal relaxation times (T1) were measured at 400 and 200 MHz. From the T1 frequency dependence, effective rotational correlation times ranging from 2.3 × 10−10 to 3.0 × 10−10 s were calculated for H-5, H-9, H-11, and H-15. This indicates that the portion of the molecule encompassed by these protons has a longer correlation time than is observed for the C-2 and the C-17 to C-19 protons, for which the average correlation time is 1.2 × 10−10 s. Hence the aliphatic side chains have more segmental motion.

Some Recent Developments in High Resolution Nuclear Magnetic Resonance

1972 ◽  
Vol 26 (4) ◽  
pp. 421-430 ◽  
Author(s):  
Edwin D. Becker
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
Nuclear Overhauser Effect ◽  
Double Resonance ◽  
Relaxation Times ◽  
Nuclear Magnetic Resonance Spectra ◽  
Recent Developments ◽  
Nuclear Overhauser ◽  
Nuclear Magnetic

Techniques for studying high resolution nuclear magnetic resonance spectra have been considerably broadened in recent years. The most far reaching development—pulse Fourier transform (FT) methods—is discussed in detail. Applications of FT techniques to measurement of relaxation times and to enhancement of weak signals, especially from natural abundance 13C, are reviewed. Double resonance methods, particularly the nuclear Overhauser effect, and the use of lanthanide shift reagents are also covered in this “mini-review.”

Homonuclear one- and two-dimensional nuclear Overhauser effect experiments and spin-echo correlated spectroscopy. Application to prostaglandin E1 and 6-keto-prostaglandin E1

1982 ◽  
Vol 60 (20) ◽  
pp. 2617-2624 ◽  
Author(s):  
George Kotovych ◽  
Gerdy H. M. Aarts
Keyword(s):  
Magnetic Resonance ◽  
Prostaglandin E1 ◽  
Nuclear Overhauser Effect ◽  
Spin Echo ◽  
Proton Magnetic Resonance Spectrum ◽  
Prostaglandin E ◽  
Two Dimensional ◽  
One Dimensional ◽  
Overhauser Effect ◽  
Nuclear Overhauser

Nuclear Overhauser effect one-dimensional and two-dimensional nuclear magnetic resonance experiments are reported for prostaglandin E1. The two-dimensional nuclear Overhauser effect measurements are combined with spin-echo correlated spectroscopy in order to assign the complete high-field proton magnetic resonance spectrum of 6-keto-prostaglandin E1. The advantages of these two-dimensional techniques are illustrated in these studies. It is also observed that the 6-keto-prostaglandin E1 H-10α proton is substituted more readily by deuterium than are the other protons α to the keto groups.

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