Optisch aktive 3-Amino-2H-azirine als Bausteine für enantiomerenreine α,α-disubstituierte α-Aminosäuren: Synthese des α-Methylphenylalanin-Synthons and Einbau in Modell-Peptide

✍ Scribed by Christoph B. Bucher; Anthony Linden; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: German
• Weight: 693 KB
• Volume: 78
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19950780416

✦ Synopsis

Optically Active 3-Amino-ZH-azirines as Synthons for Enantiomerically Pure a,a-Disubstituted a-Amino Acids:

Synthesis of the a-Methylphenylalanine Synthons and Some Model Peptides

The synthesis of a novel 2-benzyl-2-methyl-3-amino-ZH-azirine derivative with a chiral amino group is described. Chromatographic separation of the didstereoisomer mixture yielded the pure diastereoisomers 9a and 9b (Scheme 4 ) which are the D-and L-2-methylphenylalanine ((a -Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z-leucine yielded the monothiodiamides 10a and 10h (Scheme 5) and the dipeptide derivatives l l a and l l h (Scheme 6), respectively. Methanolysis of l l b yielded 12b. The absolute configuration of 10a was established by X-ray crystallography. The absolute configuration of (a-Me)Phe in 1Zb has been deduced from the known configuration of L-leucine. ') Teil der geplanten Dissertation von C. B. B. *) Die I H-NMR-Spektren beider I'erbiudungen in CDC1, zeigen bei 300 K keine scharfen Signale. Erst bei 3 1 8 K tritt bei einigen Signalen KoalerLenz ein.