Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis

Jost M, Sonke T, Kaptein B, Broxterman QB, Sewald N (2005)
SYNTHESIS 2005(02): 272-278.

Journal Article | Published | English

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Abstract
alpha-Azido carboxylic acids have recently emerged as versatile N-protected equivalents for alpha-amino acids, especially valuable when the sterically hindered C-u-dialkylated alpha-amino acids have to be incorporated. Unsymmetrically substituted C-u-dialkylated alpha-azido carboxylic acids can be obtained in enantiomerically pure form by enzymatic resolution of alpha-azido carboxamides. A L-amidase from Ochrobactrum anthropi NCIMB 40321 accepts 2-azido-2,4-dimethylpentanamide as the substrate and provides both the corresponding S-configured alpha-azido carboxylic acid and the R-configured alpha-azido carboxamide in excellent enantiomeric purity. The former is a valuable synthetic precursor of alpha-methylleucine [(alpha-Me)Leu] in peptide synthesis, as demonstrated by the successful synthesis of a (alpha-Me)Leu containing efrapeptin C analogue.
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Jost M, Sonke T, Kaptein B, Broxterman QB, Sewald N. Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis. SYNTHESIS. 2005;2005(02):272-278.
Jost, M., Sonke, T., Kaptein, B., Broxterman, Q. B., & Sewald, N. (2005). Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis. SYNTHESIS, 2005(02), 272-278.
Jost, M., Sonke, T., Kaptein, B., Broxterman, Q. B., and Sewald, N. (2005). Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis. SYNTHESIS 2005, 272-278.
Jost, M., et al., 2005. Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis. SYNTHESIS, 2005(02), p 272-278.
M. Jost, et al., “Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis”, SYNTHESIS, vol. 2005, 2005, pp. 272-278.
Jost, M., Sonke, T., Kaptein, B., Broxterman, Q.B., Sewald, N.: Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis. SYNTHESIS. 2005, 272-278 (2005).
Jost, M, Sonke, T, Kaptein, B, Broxterman, QB, and Sewald, Norbert. “Synthesis and enzymatic resolution of C-alpha-dialkylated alpha-azido carbox-amides: New enantiopure alpha-azido acids as building blocks in peptide synthesis”. SYNTHESIS 2005.02 (2005): 272-278.
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