Enzymatic desymmetrization of 2,5-dideoxystreptamine precursors

The stereoselective enzymatic acylation of meso-6,7-diazabicyclo[3.2.1]oct-6-ene-2,4-diol 4 and meso-4,6-diazidocyclohexane-1,3-diol 5 in organic media gave the corresponding monoesters in high enantiomeric excess. The hydrolysis of the corresponding diacetate derivatives in the presence of a differ...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 17; no. 6; pp. 1017 - 1021
Main Authors Chênevert, Robert, Jacques, Frédéric
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.03.2006
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
2-DEOXYSTREPTAMINE
DESIGN
INHIBITION
AMINOGLYCOSIDE
RNA
ANTIBACTERIAL ACTIVITY
AMINOCYCLITOLS
CHEMISTRY
NEOMYCIN
BINDING
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Summary:The stereoselective enzymatic acylation of meso-6,7-diazabicyclo[3.2.1]oct-6-ene-2,4-diol 4 and meso-4,6-diazidocyclohexane-1,3-diol 5 in organic media gave the corresponding monoesters in high enantiomeric excess. The hydrolysis of the corresponding diacetate derivatives in the presence of a different set of enzymes provided the same monoesters. The products are precursors of dideoxystreptamine, an aminocyclitol found in synthetic aminoglycoside antibiotics.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2006.03.014