Synthesis of screening substrates for the directed evolution of sialic acid aldolase: Towards tailored enzymes for the preparation of influenza a sialidase inhibitor analogues
Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 3, Issue: 9, Page: 1795-1800
2005
- 14Citations
- 22Captures
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Metrics Details
- Citations14
- Citation Indexes14
- 14
- CrossRef12
- Captures22
- Readers22
- 22
Article Description
The stereoselective synthesis of two epimeric screening substrates, (4R, 5R, 6R)- and (4S, 5R, 6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid, for the directed evolution of sialic acid aldolase is described. The complementary methods relied on stereoselective indium-mediated additions of ethyl α-bromomethyl acrylate to functionalised aldehydes. With an α-hydroxy aldehyde, (2R, 3R)-2,3-dihydroxy-4-oxo butanoic acid dipropylamide, the addition was chelation controlled, and the syn product, (6R, 5R, 4S)-6-dipropylcarbamoyl-2-methylidene-4,5,6-trihydroxy-hexanoic acid ethyl ester, was obtained. In contrast, the stereochemical outcome of the addition to (2R, 3A)-N, N-dipropyl-2,3-O-isopropylidene-4-oxobutyramide was consistent with Felkin-Anh control, and the anti adduct, (4R, 5R, 6R)-6-dipropylcarbamoyl-2- methylidene-4-hydroxy-5,6-O-isopropylidene-hexanoic acid ethyl ester, was the major product. Ozonolysis and deprotection gave the screening substrates as mixtures of furanose and pyranose forms, in good yields. © The Royal Society of Chemistry 2005.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=18844391810&origin=inward; http://dx.doi.org/10.1039/b501503k; http://www.ncbi.nlm.nih.gov/pubmed/15858666; https://xlink.rsc.org/?DOI=b501503k; https://dx.doi.org/10.1039/b501503k; https://pubs.rsc.org/en/content/articlelanding/2005/ob/b501503k
Royal Society of Chemistry (RSC)
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