Building units for N-backbone cyclic peptides. Part 4.1Synthesis of protected Nα-functionalized alkyl aminoacids by reductive alkylation of natural amino acids

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

doi:10.1039/A608389G

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Building units for N-backbone cyclic peptides. Part 4.¹ Synthesis of protected N^α-functionalized alkyl amino acids by reductive alkylation of natural amino acids

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

Abstract

A new method for the synthesis of protected N^α-(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.

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DOI: https://doi.org/10.1039/A608389G
Article type: Paper

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J. Chem. Soc., Perkin Trans. 1, 1997, 1501-1510

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Building units for N-backbone cyclic peptides. Part 4.¹ Synthesis of protected N^α-functionalized alkyl amino acids by reductive alkylation of natural amino acids

G. Bitan, D. Muller, R. Kasher, E. V. Gluhov and C. Gilon, J. Chem. Soc., Perkin Trans. 1, 1997, 1501 DOI: 10.1039/A608389G

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Journal of the Chemical Society, Perkin Transactions 1

Building units for N-backbone cyclic peptides. Part 4.¹ Synthesis of protected N^α-functionalized alkyl amino acids by reductive alkylation of natural amino acids

Abstract

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Building units for N-backbone cyclic peptides. Part 4.¹ Synthesis of protected N^α-functionalized alkyl amino acids by reductive alkylation of natural amino acids

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Journal of the Chemical Society, Perkin Transactions 1