Enterobactin compounds

Details Enterobactin compounds Enterobactin compounds

1993-08-25

1995-05-02

Nutter, Nathan M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 172, 536 179, C07H 1500, C07H 1700, C07H 1702

Patent

active

054120802

ABSTRACT:
Enterobactin analogs prepared from scyllo-inositol mono-orthoformate and having the following formula: ##STR1## wherein each X.sub.1, X.sub.2 and X.sub.3, independently, is H, C.sub.1-20 alkyl, phenyl, naphthyl, C.sub.7-20 aralkyl, or C.sub.7-20 alkaryl; Y is H, C.sub.1-20 alkyl, phenyl, naphthyl; C.sub.7-20 aralkyl, C.sub.7-20 alkaryl; --(C.sub.p H.sub.2p)--CH.sub.2 OH, --(C.sub.p H.sub.2p)--COOH or its salt, --(C.sub.p H.sub.2p)--NR.sub.1.R.sub.2 or its salt, or --(C.sub.p H.sub.2p)--N.sup.+ R.sub.1.R.sub.2.R.sub.3 ; in which p is 1-20 and each R.sub.1, R.sub.2 and R.sub.3, independently, is H or C.sub.1-5 alkyl; and m, n and o, independently, is 1-6; or the enantiomer thereof.

REFERENCES:
Harris et al. "Coordination Chemistry of Microbial Iron Transport Compounds, 19, Stability Constants and Electrochemical Behavior of Ferric Enterobactin and Model Complexes" Journal of the American Chemical Society, Sep. 1979, vol. 101, No. 20, pp. 6097-6104.
H. W. Lee, et al., J. Org. Chem., 50:4402-4404, 1985.
M. Miller et al., Acc. Chem. Res., 26:241-249, 1993.
F. Weitl et al., J. Org. Chem. 46:5234-5237, 1981.
M. Kappel, et al., Inorg. Chem. 24:2447-2452, 1985.

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