Stereodivergent synthesis of both (2S)- and (2R)-1-monoricinolein derivatives by lipase-catalyzed hydrolysis or transesterification directed to new ferroelectric liquid crystals

Hachiya, Iwao; Sugiura, Yoshihumi; Araki, Hiromasa; Inaoka, Osamu; Shimizu, Makoto; Akita, Masatsugu; Hamaguchi, Takashi

doi:10.1016/j.tetasy.2007.04.009

Cited by 5 publications

(2 citation statements)

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“…This property of lipase has been shown for hydrolysis reactions14 as well as acetylation15 and transesterification reactions 16. For example, PS lipase from Amano was reported to give a higher diastereoisomeric excess ( de ) than AK lipase (62 % < de < 96 %) 16. Finally, Mucor miehei lipase, which was used in this study, successfully catalysed the synthesis of monoacylglycerol with a diastereoisomeric excess superior to 99 % 17.…”

Section: Introductionmentioning

confidence: 61%

“…According to the literature, the transesterification catalysed by lipase may be diastereospecific. This property of lipase has been shown for hydrolysis reactions14 as well as acetylation15 and transesterification reactions 16. For example, PS lipase from Amano was reported to give a higher diastereoisomeric excess ( de ) than AK lipase (62 % < de < 96 %) 16.…”

Section: Introductionmentioning

confidence: 88%

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Diesterification of 3‐[(β‐Cyclodextrinyl)succinamido]propane‐1,2‐diol Catalysed by Lipase: Diastereoselectivity or Tridimensional Substrate Specificity?

et al. 2014

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The transesterification of 3‐[(β‐cyclodextrinyl)succinamido]propane‐1,2‐diol with fatty esters catalyzed by immobilized lipase from Mucor miehei occurred with very different conversions of the two diastereoisomers [(R)‐ or (S)‐amidopropanediol]. The highest conversion observed with the (S)‐amidopropanediol can be related to either lipase diastereoselectivity or substrate specificity. To investigate the diastereoselectivity of the lipase, diastereoisomers of the methylated β‐cyclodextrin were replaced by methylated glucopyranoside or methylleucine. No discrimation of the diastereoisomers by lipase was observed. Molecular modeling was performed to assess the lipase selectivity towards the two diastereoisomers. It was found that the (R)‐amidopropanediol is stabilized by hydrogen bonding with the cyclodextrin rim resulting in less reactive hydroxy groups.

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