Use of triphenylmethyl (trityl) amino protecting group in the synthesis of ketomethylene analogues of peptides

RODNEY L. JOHNSON, ROBERT B. MILLER

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9 Scopus citations

Abstract

The Grignard reagents of 2‐(2‐bromoethyl)‐1,3‐dioxane and 2‐(2‐bromoethyl)‐1,3‐dioxolane readily reacted with the 2‐thiopyridyl ester of N‐triphenylmethyl‐l‐leucine to give the ketone adducts 2‐[3‐oxo‐4(S)‐(triphenylmethyl) amino‐6‐methylheptyl]‐1,3‐dioxane (8a) and 2‐[3‐oxo‐4(S)‐(triphenylmethyl) amino‐6‐methylheptyl]‐1,3‐dioxolane (8b) in near quantitative yield. When 1 equiv. of the Grignard reagent of 2‐(2‐bromoethyl)‐1,3 dioxane was used, the desired ketone adduct 8a was formed slowly but quantitatively. In contrast, when 2 equiv. of the Grignard reagent were used, the formation of ketone 8a was instantaneous. The triphenylmethyl protecting group was easily removed from 8a using dilute acid to give the amino ketone 2‐[3‐oxo‐4(S)‐amino‐6‐methylheptyl]‐1,3‐dioxane oxalate salt (9). This material served as a useful intermediate in the synthesis of the ketomethylene analogues of the peptides, Z‐Pro‐Leu‐Gly‐OH and Leu‐Gly‐Val‐Phe‐OCH3.

Original languageEnglish (US)
Pages (from-to)581-590
Number of pages10
JournalInternational Journal of Peptide and Protein Research
Volume23
Issue number6
DOIs
StatePublished - Jun 1984

Keywords

  • 2‐thiopyridyl esters
  • Grignard reagents
  • ketomethylene analogues of peptides
  • triphenylmethyl protecting group
  • trityl protecting group

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