title: Synthesis of isotopically labeled versions of L-MTP-PE (mifamurtide) and MDP.
abstract: L-MTP-PE (1), an immunomodulator and its metabolite MDP (4) were synthesized from labeled l-alanine and its protected derivative, respectively. The key intermediate product for the labeled L-MTP-PE synthesis, [(13) C3 ,D4 ]-alanyl-cephalin (2A), was synthesized from [(13) C3 ,D4 ]-l-alanine (3A) in three steps. The key intermediate product for labeled MDP synthesis, amine 11, was prepared from [(13) C3 ,(15) N]-Boc-l-alanine (5A) in two steps.
authors.affiliation: Department of Drug Metabolism and Pharmacokinetics, Isotope Chemistry Group, Millennium Pharmaceuticals, Inc., 40 Landsdowne Street, Cambridge, MA, 02139, USA.
authors.forename: Yuexian
authors.initials: Y
authors.lastname: Li
authors.forename: Mihaela
authors.initials: M
authors.lastname: Plesescu
authors.forename: Shimoga R
authors.initials: SR
authors.lastname: Prakash
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D060326:Chemistry Techniques, Synthetic; D007553:Isotope Labeling; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
chemical_list: D010714:Phosphatidylethanolamines; C037144:mifamurtide; D000119:Acetylmuramyl-Alanyl-Isoglutamine
keywords: [13C3,15N]-Boc-l-alanine; [13C3,15N]-MDP; [13C3,D4]-L-MTP-PE; [13C3,D4]-alanyl-cephalin; [13C3,D4]-l-alanine