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Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids |
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| Authors: | Martin J O'Donnell |
| Institution: | Department of Chemistry, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202, USA |
| Abstract: | Alkylation of the benzophenone imine of glycine Wang resin with α,ω-dihaloalkanes yielded valuable reactive intermediates. These racemic ω-chloro or ω-bromo intermediates were converted to α-amino acids containing diverse side-chain functionalities (e.g. ω-chlorides, nitriles, and thioethers), proline and its ring homologs, and 1-aminocycloalkanecarboxylic acid derivatives. |
| Keywords: | alkylation combinatorial chemistry α ω-dihaloalkanes nucleophilic substitution proline homologs Schiff base activation side-chain diversity spirocyclic amino acids |
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