An efficient synthesis of a doxorubicin-peptide conjugate

Yao Jun Shi, Mark Cameron, Ulf H. Dolling, David R. Lieberman, Joseph E. Lynch, Robert A. Reamer, Michael A. Robbins, R. P. Volante, Paul J. Reider

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

An efficient synthesis of the sodium salt of the doxorubicin-peptide conjugate 1, useful for the treatment of prostate cancer is described. The EDC-mediated amide formation between the heptapeptide 4 and doxorubicin (2) as the key step has been extensively studied employing peptide-coupling additives, such as 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt) and 2-hydroxypyridine N-oxide (HOPO), surprisingly, mixing the additives HOAt and HOPO furnished the best results.

Original languageEnglish (US)
Pages (from-to)647-650
Number of pages4
JournalSynlett
Issue number5
DOIs
StatePublished - Jan 1 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Keywords

  • Amides
  • Coupling reaction
  • Isomerization
  • Peptide conjugate
  • Protecting group

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