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Synlett 1991; 1991(4): 222-224
DOI: 10.1055/s-1991-20684
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Synthesis of a Conformationally Constrained Analog of N-Acetylmuramyl Dipeptide (MDP)

Stephen Hanessian* , Virginie Ratovelomanana
  • *Department of Chemistry, Université de Montréal, C.P. 6128, Succ. A, Montréal, Québec, H3C 3J7, Canada
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Publication Date:
07 March 2002 (online)

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The C-terminal D-isoglutamine residue in N-acetylmuramyl dipeptide (MDP; N-acetylmuramyl-L-alanyl-D-isoglutamine) was replaced by a branched D-prolyl moiety, in order to mimic portions of MDP and the corresponding α-methyl and α,γ-dimethyl esters which are known to maintain their immunostimulant activity. The novel analog 4 was prepared from D-2-pyrrolidone-5-carboxylic acid. The key steps were cyclization, conjugate additions, reductive ring opening and a series of peptide couplings.

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