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Synthesis and conformational features of topographically constrained designer chimeric amino acids: The β-isopropyl phenylalanines

✍ Scribed by Subo Liao; Mark D. Shenderovich; Jun Lin; Victor J. Hruby

Book ID: 104208206
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 954 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)10127-2

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✦ Synopsis

All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, ~-isopropylphenylalanine or ~-phenylleucine, were asymmetrically synthesized in five to six steps in 20 -25% overall yield. Computer-assisted molecular modeling revealed that the ~-isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations.

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