Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, D-37077 Göttingen, Germany.
J Pept Sci. 2010 Jan;16(1):10-4. doi: 10.1002/psc.1202.
Peptide azides acquired growing impact because of application in bioconjugation via 'click chemistry' or Staudinger ligation. Furthermore, there are many methods established in organic synthesis addressing the reduction of azides to amines, but no observation of a reductive transformation of peptide azides during SPPS cleavage was yet reported. In the present study, the reduction of peptide azides during SPPS cleavage was investigated depending on the choice of thioscavenger, reacting as reductive species. First observed for short PNA/peptide conjugates the occurring extensive side reaction was also validated for one of the applied azide amino acid building blocks and was further investigated by applying different cleavage cocktails to a series of peptides varying in hydrophobicity and position of the azide moiety in the oligomer sequence.
肽叠氮化物由于在通过“点击化学”或 Staudinger 连接的生物偶联中的应用而获得了越来越大的影响。此外，有机合成中已经建立了许多方法来解决叠氮化物还原为胺的问题，但尚未有报道观察到固相多肽合成（SPPS）切割过程中肽叠氮化物的还原转化。在本研究中，根据作为还原物种反应的硫代清除剂的选择，研究了 SPPS 切割过程中肽叠氮化物的还原。该反应首先在短的 PNA/肽缀合物中观察到，并且对于所应用的叠氮氨基酸砌块之一也进行了验证，并通过将不同的切割鸡尾酒应用于一系列疏水性不同的肽以及在寡聚物序列中叠氮部分的位置不同的肽来进一步研究。
