Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids

Gal Bitan, Dan Muller, Ron Kasher, Evgenia V. Gluhov, Chaim Gilon

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36 Scopus citations

Abstract

A new method for the synthesis of protected Nα-(ω-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the α-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.

Original languageEnglish
Pages (from-to)1501-1510
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number10
DOIs
StatePublished - 21 May 1997
Externally publishedYes

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