Formation and instability of o-phthalaldehyde derivatives of amino acids.
o-Phthalaldehyde reacts with amino acids in the presence of a thiol to give highly fluorescent 1-alkyl-thio-2-alkyl-substituted isoindoles. However, the instability of the derivatives limits the general utility of the reaction. Mechanistic descriptions of isoindole formation and degradation proposed in the last years, which permit a better understanding of the factors affecting isoindole stability, are presented. The use of alternative thiols and o-phthalaldehyde-like reagents is also reviewed.
García Alvarez-Coque
M C
MC
Departamento de Química Analítica, Facultad de Química, Universidad de Valencia, Spain.
Medina Hernández
M J
MJ
Villanueva Camañas
R M
RM
Mongay Fernández
C
C
D000447:Aldehydes / Q000378:metabolism*; D000596:Amino Acids / Q000378:metabolism*; D007211:Indoles / Q000378:metabolism*; D009764:o-Phthalaldehyde / Q000378:metabolism*
D000447:Aldehydes; D000596:Amino Acids; D007211:Indoles; D009764:o-Phthalaldehyde