Conversion of l-rhamnose into ten of the sixteen 1- and 6-deoxyketohexoses in water with three reagents: d-tagatose-3-epimerase equilibrates C3 epimers of deoxyketoses

l-Rhamnose to ten of the sixteen 1- and 6-deoxy-ketohexoses by (i) Ni, H 2; (ii) Enterobacter aerogenes IK7; (iii) d-tagatose-3-epimerase. The efficient isomerization of l-rhamnose [the only cheaply available deoxy hexose] to 1-deoxy- l-psicose, 1-deoxy- d-psicose, 1-deoxy- l-fructose, 1-deoxy- d-fr...

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Bibliographic Details
Published in:Tetrahedron letters 2010-02, Vol.51 (6), p.895-898
Main Authors: Gullapalli, Pushpakiran, Yoshihara, Akihide, Morimoto, Kenji, Rao, Devendar, Akimitsu, Kazuya, Jenkinson, Sarah F., Fleet, George W.J., Izumori, Ken
Format: Article
Language:English
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Summary:l-Rhamnose to ten of the sixteen 1- and 6-deoxy-ketohexoses by (i) Ni, H 2; (ii) Enterobacter aerogenes IK7; (iii) d-tagatose-3-epimerase. The efficient isomerization of l-rhamnose [the only cheaply available deoxy hexose] to 1-deoxy- l-psicose, 1-deoxy- d-psicose, 1-deoxy- l-fructose, 1-deoxy- d-fructose, 1-deoxy- l-tagatose, 6-deoxy- l-psicose, 6-deoxy- d-psicose, 6-deoxy- l-fructose, 6-deoxy- d-fructose, and 6-deoxy- l-tagatose is described. The conversion of rhamnose to ten of the sixteen 1- and 6-deoxyketohexoses is accomplished in water in three steps. The range of substrates for d-tagatose-3-epimerase (DTE) is extended to 1- and 6-deoxyketoses. An authentic sample of 6-deoxy- d-psicose is prepared from d-psicose.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.12.024