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An Efficient Synthesis of Optically Pure (R)- and (S)-2-(aminomethyl)alanine ((R)- and (S)-ama) and (R)- and (S)-2-(aminomethyl)leucine ((R)- and (S)-aml)

✍ Scribed by Daniel Obrecht; Helena Karajiannis; Christian Lehmann; Peter Schönholzer; Clive Spiegler; Klaus Müller

Publisher: John Wiley and Sons
Year: 1995
Tongue: German
Weight: 783 KB
Volume: 78
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19950780317

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✦ Synopsis

An efficient synthesis of enantiomerically pure (R)and (S)-2-(aminomethyl)alanine ((R)and (S)-Ama) la and ( R ) -and (S)-2-(aminomethyl)leucine ( ( R )and (S)-Aml) l b is described (Schemes I and 2). Resolution of the racemic amino acids was achieved using L-phenylalanine cyclohexylamide (2) as chiral auxiliary. The free amino acids la, b were converted to the N'-Boc,N'-Z-protected derivatives 1 la, b (Scheme 3) ready for incorporation into peptides. Based on the three crystal structures of the diastereoisomeric peptides 8a, Sb, and 9b, the absolute configurations in both series were determined. P-Turn type-I geometries were observed for structures 8b and 9b, whereas 8a crystallized in an extended backbone conformation.

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