Activation of disulfide bond cleavage triggered by hydrophobization and lipophilization of functionalized dihydroasparagusic acid

作者：Inagaki Fuyuhiko^*; Momose Miyuki; Maruyama Naoya; Matsuura Kenkyo; Matsunaga Tsukasa; Mukai Chisato

来源：Organic and Biomolecular Chemistry, 2018, 16(23): 4320-4324.

DOI：10.1039/c8ob01055b

Concisely synthesized and functionalized dihydroasparagusic acid (DHAA) derivatives were used to show that the introduction of a hydrophobic functional group dramatically reduced air oxidation activity at the dithiol moieties and dominantly activated the cleavage of S-S bonds in proteins, presumably due to the hydrophobization and lipophilization. Notably, the reaction sites of water-reactive dithiol moieties behaved similarly to hydrophobic and lipophilic functional groups, which suggests impersonation of the reaction site.

• 出版日期2018-6-21