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Synthesis 2001(6): 0952-0956
DOI: 10.1055/s-2001-13397
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Novel O- and N-Linked Inositol Oligomers: A New Class of Unnatural Saccharide Mimics

Bernhard J. Paul, Theodore A. Martinot, Jerremey Willis, Tomas Hudlicky*
Department of Chemistry, University of Florida, PO Box 117200, Gainesville, Florida, 32611, USA
e-Mail: hudlicky@chem.ufl.edu;
Further Information

Publication History

Received 17 March 2001
Publication Date:
24 September 2004 (online)

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Abstract

Several N- as well as O-linked inositol oligomers were synthesized by a chemo-enzymatic approach. Whole-cell fermentation of bromobenzene with E. coli JM109(pDTG601) furnished a chiral cis-dienediol which was converted into its vinyl epoxide and vinyl aziridine, respectively. Two-fold epoxide/aziridine openings catalyzed by Yb(OTf)3 served as the key step in the synthesis of N-linked analogs, whereas a convergent approach furnished the O-linked inositol oligomers. Their synthesis is described and structural comparisons drawn to higher oligomers of l-chiro- and neo-inositol oligomers.

Key words

oligosaccharides - ring-opening - epoxides - aziridines - inositols

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11

The ratio of 18a:18b seems to vary considerably with the reaction scale. Although we have separated 18a and 18b to establish their regiochemistry, it is not necessary to do so for preparative runs, since both ultimately yield 20.

12

These results will be reported in an upcoming full paper.

14

All molecular modeling was performed with SPARTAN SGI version 5.1.1, available from Wavefunction Inc., on a Silicon Graphics O2.