Mattes W B, Hartley J A, Kohn K W
Biochim Biophys Acta. 1986 Oct 16;868(1):71-6. doi: 10.1016/0167-4781(86)90088-6.
The volatile, secondary amine piperidine is used in the Maxam-Gilbert chemical method of DNA sequencing to create strand breaks in DNA at sites of damaged bases. As such it is often used in generalized studies of DNA damage to identify 'alkali-labile lesions'. We confirm the mechanism proposed by Maxam and Gilbert (Maxam, A. and Gilbert, W. (1980) Methods Enzymol. 65, 499-560) by which aqueous piperidine creates strand breaks at sites of N7-guanine alkylations: alkaline conditions catalyze rupture of the C8-N9 bond, forming a formamido-pyrimidine structure which is displaced from the ribose moiety by piperidine. In keeping with this mechanism, the tertiary amine, N-methylpiperidine, does not catalyze the formation of strand breaks in alkylated DNA. Our data confirm the prediction that high pH in and of itself will not create strand breaks at sites of N7-alkylguanines.
挥发性仲胺哌啶用于DNA测序的马克萨姆-吉尔伯特化学方法中，以在受损碱基位点处造成DNA链断裂。因此，它常用于DNA损伤的一般性研究，以识别“碱不稳定损伤”。我们证实了马克萨姆和吉尔伯特提出的机制（马克萨姆，A.和吉尔伯特，W.（1980年）《酶学方法》65卷，499 - 560页），即哌啶水溶液在N7-鸟嘌呤烷基化位点处造成链断裂的机制：碱性条件催化C8-N9键断裂，形成甲酰胺基嘧啶结构，该结构被哌啶从核糖部分取代。与此机制一致，叔胺N-甲基哌啶不会催化烷基化DNA中链断裂的形成。我们的数据证实了以下预测：高pH本身不会在N7-烷基鸟嘌呤位点处造成链断裂。
