Formation of disulphide bonds in the reaction of SH group‐containing amino acids with trimethylamine N‐oxide

FEBS Letters

Zundel, Georg¹  Brzezinski, Bogumil² 

[1] Physikalisch-Chemisches Institut, Universität München, Theresienstr. 41, D-80333 Munich, Germany;Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, PL-60780 Poznan, Poland

关键词: Disulphide bond;    Cysteine ethyl ester;    Homocysteine ethyl ester;    SH-trimethylamine N-oxide;    Hydrogen bonded complex;   

DOI  :  10.1016/0014-5793(93)80681-J

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Two amino acids containing SH group (cysteine and homocysteine)+trimethylamine N-oxide systems were studied by FTIR and ¹H 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.

【 授权许可】

Unknown