Side reactions in solid phase synthesis of histidine-containing peptides. Characterization of two major impurities by sample displacement chromatography and FAB-MS.

A Pessi, V Mancini, P Filtri, L Chiappinelli
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Abstract

The flow-polyamide synthesis of a histidine-containing sequence (Ac-YDNVLDHLTGR) produced two major impurities which were isolated through Sample Displacement Chromatography and characterized by Fast Atom Bombardment-mass analysis. The impurities correspond to the sequence Ac-YDNVLDH, and to a peptide with the Asp residue cyclized to a succinimide. The latter side-reaction took place during the acetylation procedure, and demands attention where capping procedures are planned in the synthesis of Asp-His sequences.

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含组氨酸肽固相合成中的副反应。两种主要杂质的样品置换色谱和FAB-MS表征。
含组氨酸序列(Ac-YDNVLDHLTGR)的流动聚酰胺合成产生了两个主要杂质,通过样品置换色谱分离,并通过快速原子轰-质量分析对其进行了表征。这些杂质对应于Ac-YDNVLDH序列和一个Asp残基环化成琥珀酰亚胺的肽。后一种副反应发生在乙酰化过程中,需要注意在Asp-His序列合成中计划的盖帽程序。
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