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Mild Reductive Cleavage of Tryptophan and Histidine Side‐Chain Protecting Groups
Author(s) -
Maia Hernani L. S.,
Monteiro Luís S.,
Sebastião Joana
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1967::aid-ejoc1967>3.0.co;2-x
Subject(s) - chemistry , tryptophan , imidazole , histidine , indole test , side chain , methanol , cleavage (geology) , cyclic voltammetry , protecting group , nitrofuran , organic chemistry , medicinal chemistry , electrochemistry , alkyl , biochemistry , amino acid , electrode , fracture (geology) , biology , engineering , genetics , enzyme , polymer , geotechnical engineering
The activation potentials of the p ‐toluenesulfonyl and benzoyl groups as determined by cyclic voltammetry when they are linked to indole or imidazole are less negative than when these groups are linked to aliphatic amines. This makes them most suitable for side‐chain protection of tryptophan and histidine, as it allows mild selective cleavage not only by controlled‐potential electrolysis but also by chemical reduction using either magnesium in anhydrous methanol or mercury‐activated aluminum.