Lipase-catalyzed transesterification of methyl 2-substituted 3-hydroxy-4-pentenoates and its synthetic application to the taxol side chain

Synlett

Volumn , Issue 10, 2002, Pages 1665-1668

  Mandai, Tadakatsu ^a   Oshitari, Tetsuta ^a   Susowake, Masafumi ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

1,2 amino alcohols; Lipase catalyzed kinetic resolution; Syn and anti methyl 2 substituted 3 hydroxy 4 pentenoates; The taxol side chain

Indexed keywords

PACLITAXEL; TRIACYLGLYCEROL LIPASE;

ARTICLE; BIOTRANSFORMATION; DRUG SYNTHESIS; ENZYME MECHANISM; REACTION ANALYSIS; REDUCTION; TRANSESTERIFICATION;

EID: 0036403288     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34247     Document Type: Article

References (38)

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20. 3, 500 MHz): δ 2.62-2.68 (m, 1 H, CHCOO) and 4.28-4.33 (m, 1 H, CHOH) for 1b, and δ 2.58-2.63 (m, 1 H, CHCOO) and 4.14-4.20 (m, 1 H, CHOH) for 4b. The chemical shifts of the methine protons at 2- and 3-positions of 1 are generally observed in the down field compared with those of 4. Additionally, syn-racemates 1 are generally less polar than anti-racemates 4 on TLC analysis (hexane/ethyl acetate = 5:1-3: 1).
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23. The quantity of the lipase was not optimized. The lipase collected was washed with ether, dried in air for 5 min and stored below 5 °C. The lipase retains full activity and can be reused at least three times.
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