Premium
Synthesis of 5‐lodo‐ and 5‐nitro‐3‐indolyl phosphates as cytochemical substrates for acid phosphatase
Author(s) -
Rabiger Dorothy J.,
Chang Mildred Y.,
Matsukawa S.,
Tsou K. C.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070209
Subject(s) - chemistry , nitro , indigo , phosphate , hydrolysis , acid phosphatase , phosphatase , enzyme , medicinal chemistry , nuclear chemistry , organic chemistry , art , alkyl , visual arts
The synthesis of 5‐iodo‐3‐indolyl and 5‐nitro‐3‐indolyl phosphate for cytochemical demonstration of acid phosphatase is reported. Enzymatic hydrolysis of these compounds liberates the corresponding indoxyl which is oxidized to the substituted indigo at an acid p H. In contrast, the 5‐bromo and the unsubstituted indoxyl are not oxidized readily at an acid p H. Comparison of the UV and visible, spectra of the disubstituted indigo has offered a partial explanation for this difference. E.S.R. measurements showed that 5,5′‐diiodoindigo, unlike 5,5′‐dibromoindigo, gives a detectable radical ion at an acid p H.