Synthesis of isotopically labeled versions of L-MTP-PE (mifamurtide) and MDP.

Yuexian Li, Mihaela Plesescu, Shimoga R Prakash
Author Information
  1. Yuexian Li: Department of Drug Metabolism and Pharmacokinetics, Isotope Chemistry Group, Millennium Pharmaceuticals, Inc., 40 Landsdowne Street, Cambridge, MA, 02139, USA.

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.

Keywords

MeSH Term

Acetylmuramyl-Alanyl-Isoglutamine
Chemistry Techniques, Synthetic
Isotope Labeling
Phosphatidylethanolamines

Chemicals

Phosphatidylethanolamines
mifamurtide
Acetylmuramyl-Alanyl-Isoglutamine

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