Solid-phase S-3CR generates N-substituted α-aminonitriles for the synthesis of α-phenyl-α-(1-piperazinyl) substituted amino acids

Probst, Katrin C. and Jung, G. 2006. Solid-phase S-3CR generates N-substituted α-aminonitriles for the synthesis of α-phenyl-α-(1-piperazinyl) substituted amino acids. Amino Acids 30 (3) , pp. 243-250. 10.1007/s00726-006-0285-2

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Abstract

Structurally diverse amino acids were prepared as versatile synthons for combinatorial chemistry. Using an optimized solid-phase synthesis by Strecker-three-component-reaction (S-3CR), two different polymer linker constructs carrying piperazine were investigated. (a) Acrylate derived base-labile linker yielded α-aminonitriles with N-alkylated piperazines via Hofmann elimination after quarternisation with an alkyl halide. The crude product purities were in the range of 54–87%. (b) A urethane type linker yielded α-aminonitriles with the free piperazine nitrogen when cleaved with acid and the product purities were 72–93%. The α-aminonitriles were easily converted to novel Nɛ – Fmoc-protected α-amino acids with α-(1-piperazinyl) and α-phenyl substituents.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Medicine
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Amino acid synthesi; Strecker reaction; Solid-phase synthesis; Combinatorial chemistry; Multicomponent reaction
Publisher:	Springer
ISSN:	0939-4451
Last Modified:	31 Jan 2020 04:15
URI:	https://orca.cardiff.ac.uk/id/eprint/96506

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