Genepep SA, Les Coteaux Saint Roch, 12 Rue du Fer à Cheval, 34430 St Jean de Védas, France.
Amino Acids. 2013 Feb;44(2):733-42. doi: 10.1007/s00726-012-1397-5. Epub 2012 Sep 12.
A large number of bioactive peptides are cyclized through a disulfide bridge. This structural feature is very important for both bioactivity and stability. The oxidation of cysteine side chains is challenging not only to avoid intermolecular reaction leading to oligomers and oxidation of other residues but also to remove solvents and oxidant such as dimethyl sulfoxide. Supported reagents advantageously simplify the work-up of such disulfide bond formation, but may lead to a significant decrease in yield of the oxidized product. In this study, two resins working through different mechanisms were evaluated: Clear-Ox, a supported version of Ellman's reagent and Oxyfold, consisting in a series of oxidized methionine residues. The choice of the supported reagent is discussed on the light of reaction speed, side-products formation and yield considerations.
大量的生物活性肽通过二硫键环化。这种结构特征对于生物活性和稳定性都非常重要。半胱氨酸侧链的氧化不仅具有挑战性，因为它需要避免导致低聚物和其他残基氧化的分子间反应，还需要去除溶剂和氧化剂，如二甲基亚砜。支持试剂有利地简化了这种二硫键形成的后处理，但可能导致氧化产物的产率显著降低。在这项研究中，评估了两种通过不同机制起作用的树脂：Clear-Ox，一种 Ellman 试剂的支持版本，和 Oxyfold，由一系列氧化的蛋氨酸残基组成。根据反应速度、副产物形成和产率考虑，讨论了支持试剂的选择。
