Sidorova M V, Kudriavtseva E V, Antopol'skiĭ M L, Pal'keeva M E, Ovchinnikov M V, Bespalova Zh D
Bioorg Khim. 1996 Apr;22(4):273-9.
A simple, rapid, and highly efficient method for intramolecular disulfide formation in tryptophan-containing peptides using hydrogen peroxide was elaborated. Solid phase synthesis of the peptide fragment corresponding to 601-617 sequence of transmembrane gp41 glycoprotein of HIV-1 was performed by Fmoc-technique. Coupling of Fmoc-Asn-OH by DCC-HOBt method was shown to be accompanied by a side reaction of dehydration of asparagine amide function with the formation of side product (22%) containing 3-cyanoalanine residue. This side reaction was not observed, when Fmoc-Asn-OH was coupled in the form of its p-nitrophenyl ester and with HOBt as a catalyst.
阐述了一种使用过氧化氢在含色氨酸的肽中形成分子内二硫键的简单、快速且高效的方法。采用Fmoc技术进行了HIV-1跨膜糖蛋白gp41 601-617序列对应肽片段的固相合成。通过DCC-HOBt法偶联Fmoc-Asn-OH时，天冬酰胺酰胺官能团脱水形成含3-氰基丙氨酸残基的副产物（22%）的副反应被观察到。当Fmoc-Asn-OH以其对硝基苯酯形式并以HOBt作为催化剂进行偶联时，未观察到该副反应。
