✦ LIBER ✦
Reversible derivatization to enhance enzymatic synthesis: Chemoenzymatic synthesis of doxorubicin-14-O-esters
✍ Scribed by Ian C. Cotterill; Joseph O. Rich; Marc D. Scholten; Lyudmila Mozhaeva; Peter C. Michels
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 122 KB
- Volume
- 101
- Category
- Article
- ISSN
- 0006-3592
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✦ Synopsis
Abstract
An efficient three‐step, chemoenzymatic synthesis of unprotected doxorubicin‐14‐O‐esters from doxorubicin hydrochloride salt is described. The key step is a lipase‐catalyzed regioselective transesterification/esterification using commercially available acyl donors and doxorubicin reversibly derivatized with N‐alloc to improve substrate loadings. The overall yield is ca. 60% and chromatographic purification is not required, thereby making the process more amenable to scale‐up. Biotechnol. Bioeng. 2008;101: 435–440. © 2008 Wiley Periodicals, Inc.