160397-99-9Relevant academic research and scientific papers
Synthesis of (+)-(4S)- and (-)-(4R)-(11Z)-4-hydroxyretinals and determination of the absolute stereochemistry of a visual pigment chromophore in the firefly squid, Watasenia scintillans
Katsuta,Ito,Yoshihara,Nakanishi,Kikkawa,Fujiwara
, p. 6917 - 6921 (1994)
First syntheses of (+)-(4S)- and (-)-(4R)-(11Z)-4-hydroxyretinals (4-OH-RALs) (4a and 4b) were accomplished from (4S)- and (4R)-4-hydroxy-β-ionones, respectively, to determine the absolute configuration of a visual pigment chromophore in Watasenia scintillans, which has been isolated as a new chromophore in the animal kingdom. The CD spectra of the native chromophore and its anti-oxime agreed with those of synthetic (4R)-compounds. Application of the CD exciton chirality method to the p-(dimethylamino)cinnamate of (4R)-4-OH-RAL also established the absolute configuration of the native chromophore as 4b.
Synthesis of enantiopure C3- and C4-hydroxyretinals and their enzymatic reduction by ADH8 from Xenopus laevis
Dominguez, Marta,Alvarez, Rosana,Borras, Emma,Farres, Jaume,Pares, Xavier,De Lera, Angel R.
, p. 155 - 164 (2007/10/03)
(R)-all-trans-3-hydroxyretinal 1, (S)-all-trans-4-hydroxyretinal 3 and (R)-all-trans-4-hydroxyretinal 5 have been synthesized stereoselectively by Horner-Wadsworth-Emmons and Stille cross-coupling as bond-forming reactions. The CBS method of ketone reduct
