Novel O- and N-linked inositol oligomers: A new class of unnatural saccharide mimics

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