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Formation of disulphide bonds in the reaction of SH group‐containing amino acids with trimethylamine N‐oxide
Author(s) -
Brzezinski Bogumil,
Zundel Georg
Publication year - 1993
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(93)80681-j
Subject(s) - trimethylamine , chemistry , group (periodic table) , oxide , trimethylamine n oxide , amino acid , medicinal chemistry , polymer chemistry , organic chemistry , biochemistry
Two amino acids containing SH group (cysteine and homocysteine)+trimethylamine N‐oxide systems were studied by FTIR and 1 H NMR spectroscopy. This study demonstrates that cysteine and homocysteine ethylesters react with trimethylamine N‐oxide. Immediately after mixing, SH⋯ON ⇋ S − ⋯H + ON hydrogen bonds with large proton polarizability are formed. Then a reaction proceeds resulting in the formation of corresponding disulphides. Trimethylamine N‐oxide is present in biological systems. Thus, our results suggest that trimethylamine N‐oxide may play a regulatory role in S‐S bond formation in enzymes and other proteins.