A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.
3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol. The alcohol was converted to 3-(alpha-iodo-p-tolyl)-3-(trifluoromethyl)-3H-diazirine, which was used to alkylate N-(diphenylmethylene)glycine ethyl ester. After deprotection the amino acid was obtained with an overall yield of 18%. The D- and L-isomers of 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine have also been resolved, and 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine labeled with tritium has been prepared. The advantages of using this amino acid as a building block for peptide photoaffinity reagents is discussed.
D000345:Affinity Labels / Q000138:chemical synthesis*; D001389:Azirines / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000032:analysis; D010455:Peptides; D010649:Phenylalanine / Q000031:analogs & derivatives; D010777:Photochemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000345:Affinity Labels; D001389:Azirines; D006838:Hydrocarbons; D010455:Peptides; C030011:carbene; D010649:Phenylalanine; C044966:3-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)alanine; D008697:Methane