Enantioselective Synthesis of a Phenylalanine Library Containing Alkyl Groups on the Aromatic Moiety: Confirmation of Stereostructure by X-Ray Analysis

• Published in: Chemical & Pharmaceutical Bulletin Vol. 54; no. 6; pp. 873 - 877
• Main Authors: Li, Tingyou, Tsuda, Yuko, Minoura, Katsuhiko, In, Yasuko, Ishida, Toshimasa, Lazarus, Lawrence H., Okada, Yoshio
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 2006; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan
• Subjects: Alkylation; asymmetrical hydrogenation; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Crystallography, X-Ray; enzymatic digestion; Hydrocarbons, Aromatic - chemistry; L-configuration; Life Sciences & Biomedicine; Molecular Structure; Nanostructures; Particle Size; Pharmacology & Pharmacy; Phenylalanine - analogs & derivatives; Phenylalanine - chemical synthesis; phenylalanine analogue; Physical Sciences; Science & Technology; Stereoisomerism; Substrate Specificity; X-ray analysis; X-Rays; DESIGN; ASYMMETRIC-SYNTHESIS; asymmetrical hydrogenation; ANALOGS; L-configuration; DMP; OPIOID RECEPTOR AFFINITY; enzymatic digestion; PEPTIDES; AMINO-ACIDS; X-ray analysis; RESIDUE; SELECTIVITY; DERIVATIVES; phenylalanine analogue
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.54.873

Six phenylalanine analogues containing 2′-methyl-, 2′,6′-dimethyl-, 2′-ethyl-6′-methyl-, 2′-isopropyl-6′-methyl-, 2′,4′,6′-trimethyl-, and 3′,5′-dimethyl-L-phenylalanine were synthesized enantioselectively through asymmetric hydrogenation of acetamidoacrylate derivatives. Enzymatic digestion and X-ray analysis supported the L-configuration of the phenylalanine derivatives obtained.