
TY  - JOUR
A1  - A Holt, Leo 
A1  - Milligan, Brian 
T1  - Reactions of I,I-Diacetoxyiodobenzene with Proteins: Conversion of Amide Side-Chains to Amines
JF  - Australian Journal of Biological Sciences
JO  - Aust. Jnl. Of Bio. Sci.
Y1  - 1981
VL  - 34
IS  - 4
SP  - 395
EP  - 400
KW  - 
UR  - https://doi.org/10.1071/BI9810395 
N2  - Experiments with the N-benzyloxycarbonyl derivatives of asparagine and glutamine as models show that, in unbuffered solutions, I,I-diacetoxyiodobenzene (1) is more effective than the corresponding trifluoroacetoxy derivative (2) for converting the amide side-chains of proteins to amines. Maximum modification of the glutamine residues of insulin and lysozyme occurs within 1-2 h of treatment with 1 in aqueous methyl cyanide at 20°C, but asparagine residues react more slowly. The amide side-chains are converted to the corresponding amines in at least 90 % yield, as shown by analysis of acid hydrolysates for aspartic acid, lX,p-diaminopropionic acid, glutamic acid and lX,y-diaminobutyric acid. Numerous side-reactions also occur, tyrosine, cystine, methionine, arginine, lysine and N-terminal residues all being modified to some extent. 
ER  -

