Simple and versatile method for tagging phenyldiazirine photophores.
The first effective method for the introduction of a versatile substituent on 3-phenyl-3-trifluoromethyldiazirine has been developed. The simple preparation of a useful aldehyde intermediate allows easy access to various elaborated photoaffinity ligands, including a l-phenylalanine analog bearing a diazirine ring (TmdPhe). The asymmetric synthesis of TmdPhe was easily accomplished in gram quantities. Site-directed incorporation of this compound into the structure of a calmodulin-binding peptide using automated peptide synthesis afforded a photoreactive peptide that was successfully used for the specific labeling of calmodulin.
Nakashima
Hiroyuki
H
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
Hashimoto
Makoto
M
Sadakane
Yutaka
Y
Tomohiro
Takenori
T
Hatanaka
Yasumaru
Y
D000595:Amino Acid Sequence; D001389:Azirines / Q000138:chemical synthesis / Q000737:chemistry; D002147:Calmodulin / Q000737:chemistry; D002148:Calmodulin-Binding Proteins / Q000737:chemistry; D003979:Diazonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D010649:Phenylalanine / Q000031:analogs & derivatives; D010777:Photochemistry
D001389:Azirines; D002147:Calmodulin; D002148:Calmodulin-Binding Proteins; D003979:Diazonium Compounds; C035176:benzenediazonium; D010649:Phenylalanine; C044966:3-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)alanine