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Synthesis of (+)-(4S)- and (−)-(4R)-11Z-4-hydroxyretinals and determination of the absolute stereochemistry of a visual pigment chromophore in the bioluminescent squid, Watasenia scintillans

✍ Scribed by Yuko Katsuta; Kazuo Yoshihara; Koji Nakanishi; Masayoshi Ito

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 279 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)75995-8

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✦ Synopsis

Syntkesis qf (+)-(4S)-and (-)-(4R)-llU-hydroxyretinak (4-OH-RALs) la and Ib was accomplishedfrorn (4S)-and (4R)-4-hydroxy-/I-ions. respectively. to determine the absolute co&tuation of a visual

pigment chromophore in Watasenia scintillans. The CD spectra qf the native chronwphore ana' its anti-okme agreed with those of synthetic (4R)-compounds. The CD exciton chirality mthod as qplied IO rhe pdimethykaminoci qf (4R)4-OH-R& also estabiishes the absoiute confisttratio~ sf the nativt chrowtqvhore as 1 b.

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