Synthesis of a Conformationally Constrained Analog ofN-Acetylmuramyl Dipeptide (MDP)
- 1 January 1991
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1991 (04) , 222-224
- https://doi.org/10.1055/s-1991-20684
Abstract
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.Keywords
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