PATIC: a conformationally constrained photoisomerizable amino acid.
The synthesis of a conformationally constrained photoisomerizable amino acid, phenylazo-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (PATIC), is described. This amino acid can be incorporated into peptides using standard Fmoc procedures and can be accommodated within alpha-helical structures albeit with some loss of stability of the structure. PATIC can serve as a useful building block for the synthesis of photoregulated peptides and proteins.
Zhang
J
J
Department of Chemistry, University of Toronto, Canada.
James
D A
DA
Woolley
G A
GA
D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D002942:Circular Dichroism; D007536:Isomerism; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010777:Photochemistry; D011487:Protein Conformation; D013056:Spectrophotometry, Ultraviolet; D044005:Tetrahydroisoquinolines
D001391:Azo Compounds; D007546:Isoquinolines; D044005:Tetrahydroisoquinolines; C121749:phenylazo-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid; C031270:1,2,3,4-tetrahydroisoquinoline carboxylic acid