The solution conformation and electronic structure of retinoids by NMR and theoretical methods
This study emphasizes the use of {sup 1}H and {sup 13}C NMR and MNDO calculations to study the conformation and electronic structure of retinoids. First, the {sup 13}C NMR chemical sifts ({delta}) of twenty-four {alpha}-and {beta}{sub 2}-retinoids were assigned by 2D heteronuclear correlated (HETCOR) NMR techniques. In the second study, a linear correlation was found between {Delta}{delta}{sub X} and the corresponding MNDO {kappa}{sup {minus}} and total charge density differences ({Delta}{sub q}) for several functional groups (CH{sub 3}, CH{sub 2}OH, CHO, and CHN(CH{sub 2}){sub 3}CH{sub 3}) except for the protonated retinylidene Schiff base (PRSB) which deviated. Two studies using {sup 1}H and {sup 13}C NMR to determine the conformation of aromatic retinoids and the retinoid-phenyl group interactions were next addressed. The {sup 1}H and {sup 13}C {delta}'s of three aromatic retinoid TTNN (tetrahydrotetramethylnaphthalenylnaphthoic acid) derivatives were determined by HETCOR and phase-sensitive 2D NOE experiments. A method was developed which related NOE signals for molecules undergoing rapid conformational changes to interproton distance. The final section determined the orientation of a phenyl ring with respect to the retinylidene Schiff base (RSB).
- Research Organization:
- Alabama Univ., Birmingham, AL (USA)
- OSTI ID:
- 7191571
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
59 BASIC BIOLOGICAL SCIENCES
BARYONS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACID ESTERS
CHEMICAL SHIFT
ELEMENTARY PARTICLES
ESTERS
EVEN-ODD NUCLEI
FERMIONS
HADRONS
IMINES
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEONS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PROTONS
RESONANCE
RETINOIC ACID
SCHIFF BASES
SPECTRA
STABLE ISOTOPES
TRACER TECHNIQUES