A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.

Journal article

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.

Authors: Shih, L; Bayley, H

• Publication status: Published
• Journal: Analytical biochemistry
• Volume: 144
• Issue: 1
• Pages: 132-141
• Publication date: 1985-01-01
• DOI: 10.1016/0003-2697(85)90094-6
• EISSN: 1096-0309
• ISSN: 0003-2697
• Language: English
• Keywords: Azirines; Stereoisomerism; Photochemistry; Peptides; Chemical Phenomena; Chemistry; Spectrophotometry, Ultraviolet; Hydrocarbons; Affinity Labels; Methane