Configurational correlation of phosphintes by nuclear magnetic resonance and optical rotatory dispersion

1967 ◽  
Vol 89 (18) ◽  
pp. 4786-4787 ◽  
Author(s):  
Robert Allen. Lewis ◽  
Olaf. Korpiun ◽  
Kurt. Mislow
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Configurational Correlation ◽  
Nuclear Magnetic

THE β-D -CONFIGURATION OF THE RIBOSYL NICOTINAMIDE PORTION OF DIPHOSPHOPYRIDINE NUCLEOTIDE

1963 ◽  
Vol 41 (4) ◽  
pp. 889-897 ◽  
Author(s):  
R. U. Lemieux ◽  
J. W. Lown
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Dispersion Curves ◽  
Optical Rotatory Dispersion ◽  
Rotatory Dispersion ◽  
Optical Rotatory ◽  
Anomeric Configuration ◽  
Anomeric Center ◽  
Nuclear Magnetic

The configurations of the anomeric N-(tetra-O-acetyl-D-glucopyranosyl)-3-carboxamido-pyridium bromides were established by nuclear magnetic resonance (n.m.r.) spectroscopy. The β-D-anomer was found to undergo deacetylation without anomerization. This compound on oxidation with periodate has been shown (M. Viscontini and E. Hürzeler-Jucker. Helv. Chim. Acta, 39, 1620 (1956)) to yield a different product than did a synthetic N- (D-ribo-furanosyl)-3-carboxamidopyridinium chloride. Therefore, the anomeric configuration of the latter compound must be is α-D. Since its anomer was used (N. A. Hughes, G. W. Kenner, and A. Todd. J. Chem. Soc. 3733 (1957)) to synthesize diphosphopyridine nucleotide (DPN), the configuration of the anomeric center in this portion of the coenzyme must be β-D. Optical rotatory dispersion curves are reported for DPN, its component nucleotides, and the above-mentioned D-glucosides.

EXCEPTIONS TO HUDSON'S RULES OF ISOROTATION: THE NUCLEAR MAGNETIC RESONANCE SPECTRA OF ANOMERIC PYRIMIDINE 2-DEOXY-D-RIBONUCLEOSIDES

1961 ◽  
Vol 39 (1) ◽  
pp. 110-115 ◽  
Author(s):  
R. U. Lemieux ◽  
M. Hoffer
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Magnetic Resonance Spectroscopy ◽  
Optical Rotatory Dispersion ◽  
Resonance Spectroscopy ◽  
Optical Rotatory ◽  
Nuclear Magnetic Resonance Spectra ◽  
Optical Rotations ◽  
Derivatives Of ◽  
Nuclear Magnetic

Nuclear magnetic resonance spectroscopy and optical rotatory dispersion measurements were used to correlate the configurations of anomeric pairs for the 1-(2-deoxy-D-ribofuranosyl) derivatives of 5-methyl- and 5-fluoro-uracil. The optical rotations of the anomers were found opposite to those expected on the basis of Hudson's rules of isorotation.

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