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A Convenient Synthesis of Muramic Acid and Other 3-O-Ethers of D-Glucosamine

Naturevolume 191pages495496 (1961) | Download Citation

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Abstract

3-O-ETHERS of D-glucosamine, including muramic acid (3-O-carboxyethyl-D-glucosamine, a component of bacterial cells walls), have been prepared1–4 from the intermediate I (R = Me or Et)5. We have applied the Williamson ether synthesis to the intermediate II (R = H)6 and have prepared muramic acid, 3-O-methyl- and 3-O-carboxymethyl-D-glucos-amines by this procedure. The intermediate (II) is readily prepared in good yield by a two-stage process, whereas the preparation of substance I requires three steps and a separation of the α and β anomers7,8.

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References

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    Jeanloz, R. W., Adv. in Carb. Chem., 13, 189 (1958).

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    Strange, R. E., and Kent, L. H., Biochem. J., 71, 333 (1959).

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    Zilliken, F., Fed. Proc., 18, 966 (1959).

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    Lambert, R., and Zilliken, F., Chem. Ber., 93, 2915 (1960).

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    Neuberger, A., J. Chem. Soc., 50 (1941).

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    Konstas, S., Photaki, I., and Zervas, L., Chem. Ber., 92, 1288 (1959).

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    Kuhn, R., Zilliken, F., and Gauhe, A., Chem. Ber., 86, 466 (1953).

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    Roth, W., and Pigman, W., J. Amer. Chem. Soc., 82, 4608 (1960).

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Affiliations

  1. National Institute for Medical Research, Mill Hill, N.W.7

    • ROY GIGG
  2. Human Nutrition Research Unit, Mill Hill, N.W.7

    • PATRICIA M. CARROLL

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https://doi.org/10.1038/191495a0

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