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By Abelson J. (ed.), Simon M. (ed.), Sies H. (ed.)

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Additional info for Retinoids: Molecular and Metabolic Aspects Part A

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3 Isler e t al. 4 at Hoffmann-La Roche developed the first synthesis of retinol on an industrial scale. In this field, there have been major advances in synthetic organic chemistry, resulting in the synthesis of about 2000 retinoids. Some have little resemblance to retinol and retinoic acid but still retain the biological activities associated with them. Structures of Retinoids The classic retinoid structure is generally subdivided into three segments, namely, the polar terminal end, the conjugated side chain, and the cyclohexenyl ring.

The detection wavelength is 328-330 nm (retinol) or 350 nm (retinoic acid). Liquid Chromatographic Conditions The conditions of the different liquid chromatographic systems used are as follows. I. 5 ml/min; temperature, ambient; injection volume, 100/zl. 2. Retinol/reversed-phase chromatographyS: 7 M. G. M. De Ruyter and A. P. De Leenheer, Clin. Chem. ) 22, 1593 (1976). s H. J. C. F. Nelis, J. De Roose, H. Vandenbavi6re, and A. P. De Leenheer, Clin. Chem. ) 29, 1431 (1983). 46 cm; mobile phase, acetonitrile : dichloromethane : methanol, 70 : 15 : 15 (v/v/v); flow rate, 1 ml/min; temperature, ambient; injection volume, 50/~1.

4 ppm upfield shift of the olefinic proton in the Z double-bond isomer relative to the equivalent signal in the E isomer, as well as smaller shifts of similar signals for the gem-dimethyl and aromatic protons caused by the greater shielding of these protons by the aromatic groups in the Z isomer. The biaryl retinoid carboxylic acids and other nonolefinic retinoids are important tools in retinoid structure-activity studies. The complete assignment of the chemical shifts for the protons in this series of retinoids requires additional techniques, which are well illustrated by the analysis of the solution conformation of 17 and 27, in which all the IH and ~3C NMR chemical shifts were unequivocally assigned using two-dimensional (2D) NMR.

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