350032-60-9Relevant articles and documents
Synthesis, structure, and biological evaluation of novel N- and O-linked diinositols
Paul, Bernhard J.,Willis, Jerremey,Martinot, Theodore A.,Ghiviriga, Ion,Abboud, Khalil A.,Hudlicky, Tomas
, p. 10416 - 10426 (2002)
Several O-and N-linked inositols and/or aminoinositols have been prepared by iterative opening of epoxides and aziridines derived from homochiral cyclohexadiene cis-diols. The three inositols and their intermediate conduritols (conduramines) were tested a
Novel O- and N-linked inositol oligomers: A new class of unnatural saccharide mimics
Paul, Bernhard J.,Martinot, Theodore A.,Willis, Jerremey,Hudlicky, Tomas
, p. 952 - 956 (2007/10/03)
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.