Synthese De La N-acetylmuramyl (OXO-14C-propyl)-L-alanyl-D-isoglutamine (MDP-14C)

SYNTHESIS OF N-ACETYLMURAMYL (14C-OXOPROPYL)-L-ALANYL-D- ISOGLUTAMINE (14C - MDP) Condensation of (1-14C) DL-2-bromopropionic acid with benzyl 2-acetamido-4,6-0-benzylidene-2-deoxy-β-D-glucopyranoside 7 in presence of sodium hydride gave 50 % of crystalline compound 3, having the correct stereochemistry of natural muramic acid. The latter, in presence of Woodward's reagent, reacted with L-alanyl-D-isoglutamine benzyl ester hydrochloride, leading to compound 4. Removal of benzylidene and benzyl groups by successive acetic acid exposure and hydrogenolysis gave rise to 2-acetamido-2-deoxy-3-0 (2-D-(14CO) propionyl-L-alanyl-D-isoglutamine)-D-glucopyranose (14C-MDP) Specific activity : 42 mCi/mMole in a 10 % overall yield based on sodium (1-14C) propionate.

[1]  E. Lederer,et al.  Synthesis of some new analogs of the immunoadjuvant glycopeptide MDP (N-acetyl-muramyl-L-alanyl-D-isoglutamine). , 2009, International journal of peptide and protein research.

[2]  J. Choay,et al.  Synthesis of N-acetyl-muramyl-L-alanyl-D-isoglutamine, an adjuvant of the immune response, and of some n-acetyl-muramyl-peptide analogs. , 2009, International journal of peptide and protein research.

[3]  F. Audibert,et al.  Distinctive adjuvanticity of synthetic analogs of mycobacterial water-soluble components. , 1976, Cellular immunology.

[4]  S. Kusumoto,et al.  Chemical Synthesis of N-Acetylmuramyl Peptides with Partial Structures of Bacterial Cell Wall and Their Analogs in Relation to Immunoadjuvant Activities , 1976 .

[5]  P. Sinaỹ,et al.  Total synthesis and adjuvant activity of bacterial peptidoglycan derivatives. , 1975, Biochemical and biophysical research communications.

[6]  E. Lederer,et al.  Minimal structural requirements for adjuvant activity of bacterial peptidoglycan derivatives. , 1974, Biochemical and biophysical research communications.

[7]  R. Jeanloz,et al.  AN IMPROVED, STEREOSELECTIVE SYNTHESIS OF 2-AMINO-3-O-(D-1-CARBOXYETHYL)-2-DEOXY-D-GLUCOSE (MURAMIC ACID). , 1965, The Journal of organic chemistry.

[8]  B. Tolbert,et al.  Synthesis of Several Carbon-14 Labeled DL-Alanines , 1952 .

[9]  W. E. TREVELYAN,et al.  Detection of Sugars on Paper Chromatograms , 1950, Nature.

[10]  S. Kusumoto,et al.  Synthesis of N-acetylmuramyl-L- [U−14C]alanyl-D-isoglutamine , 1977 .

[11]  R. Woodward,et al.  A useful synthesis of peptides , 1966 .