Enzyme‐Catalyzed Regioselective Acetylation of Functionalized Glycosides
Novozym 435 (N435) is an immobilized lipase ( Candida antarctica lipase B) capable of catalyzing transesterfications in organic media. This paper describes how this enzyme can be used for regioselective acetylation of unprotected carbohydrates providing protected monosaccharide building blocks in on...
| Published in: | European Journal of Organic Chemistry |
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| Main Authors: | , |
| Other Authors: | |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2020
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| Subjects: | |
| Online Access: | http://dx.doi.org/10.1002/ejoc.202000696 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.202000696 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.202000696/fullpdf |
| Summary: | Novozym 435 (N435) is an immobilized lipase ( Candida antarctica lipase B) capable of catalyzing transesterfications in organic media. This paper describes how this enzyme can be used for regioselective acetylation of unprotected carbohydrates providing protected monosaccharide building blocks in only one step. Unprotected thiogylcosides with both gluco, xylo , and manno stereochemistry were tolerated by the enzyme and afforded the acetylated products in high yields. The regioselective acetylation was easily scaled up to a 5.0 gram scale and in most cases, no purification was needed. Several other glycosides, including 2‐azido‐2‐deoxy glucosides, galactosides, and gluconolactones, were also acetylated and the scope and limitations using N435 has been uncovered. |
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