Synthesis and resolution of novel 3'-substituted phenylalanine amides.
A convenient approach to the synthesis of ring-substituted phenylalanine amides is described. Phase transfer alkylation of N-(diphenylmethylene)amino acetonitrile or N-(diphenylmethylene)glycine ethyl ester provides alpha-substituted imines 2 and 6. After acid hydrolysis and esterification, resolution with alpha-chymotrypsin provided 3'-substituted phenylalanine analogs 9a-d which could easily be converted to N alpha-t-butyloxycarbonyl-phenylalanine amides for use in the synthesis of peptide analogs. The approach described here is amenable to the synthesis of 3-substituted phenylalanines with a wide variety of substituents for determination of structure-activity relationships of peptides.
Knittel
J J
JJ
Division of Pharmacology and Medicinal Chemistry, College of Pharmacy, University of Cincinnati, OH 45267-0004.
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D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D010649:Phenylalanine / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship
D000577:Amides; D010649:Phenylalanine