N-{trans-2-[[2‘-(Acetylamino)cyclohexyl]oxy]acetyl}-l-alanyl-d-glutamic Acid: A Novel Immunologically Active Carbocyclic Muramyl Dipeptide Analogue
A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-{trans-2-[[2‘-(acetylamino)cyclohexyl]oxy]acetyl}-l-alanyl-d-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the d-isoglutamine residue of the MDP molecule by a trans-2-[[2‘-(acetylamino)cyclohexyl]...
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| Published in: | Journal of medicinal chemistry Vol. 41; no. 4; pp. 530 - 539 |
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| Main Authors: | , , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
12-02-1998
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| Online Access: | Get full text |
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| Summary: | A novel non-pyrogenic carbocyclic muramyl dipeptide (MDP) analogue, N-{trans-2-[[2‘-(acetylamino)cyclohexyl]oxy]acetyl}-l-alanyl-d-glutamic acid, was obtained by replacement of the N-acetylmuramic acid part and the d-isoglutamine residue of the MDP molecule by a trans-2-[[2‘-(acetylamino)cyclohexyl]oxy]acetyl moiety and d-glutamic acid, respectively. The title compound was selected as a promising candidate for further evaluation among several related analogues on the basis of an immunorestoration test in mice. This novel nor-MDP analogue protects mice against the immunosuppressive effect of cyclophosphamide and increases the nonspecific resistance of mice against fungal infection. It is an immunomodulator which enhances the maturation of lymphocytes B to plasma cells and increases the activity of lymphocytes B and lymphocytes T as well as that of macrophages but does not alter the number of these cells. |
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| Bibliography: | istex:C29436CAF5EC4DD10DE2ED01CCD628ACB706C8FC ark:/67375/TPS-5JDBCN8B-P |
| ISSN: | 0022-2623 1520-4804 |
| DOI: | 10.1021/jm970509d |