SELECTIVE LABELING OF ALPHA-AMINO OR EPSILON-AMINO GROUPS IN PEPTIDES BY THE BOLTON-HUNTER REAGENT
SELECTIVE LABELING OF ALPHA-AMINO OR EPSILON-AMINO GROUPS IN PEPTIDES BY THE BOLTON-HUNTER REAGENT
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DOI：
10.1016/0196-9781(92)90027-z
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发表时间：
1992-11-01
期刊：
影响因子：
3
通讯作者：
VINCENT, JP
中科院分区：
文献类型：
--
作者：
GAUDRIAULT, G;VINCENT, JP
将N-琥珀酰亚胺基-3（4-羟基苯基）丙酸酯（博尔顿-亨特试剂）或其I-125标记的衍生物掺入肽中，可以通过改变反应的pH值来选择性地针对α-胺或ε-胺功能。α-氨基的酰化在pH 6.5下是有利的，而ε-氨基在pH 8.5下更容易反应。我们利用这一结果，制备了两个新的I-125标记的P物质和神经降压素的类似物，选择性和可逆地结合到各自的受体。本文所述的方法具有普遍意义，可用于将各种报告基团掺入肽结构中。
Incorporation of N-succinimidyl-3(4-hydroxyphenyl) propionate (Bolton-Hunter reagent) or its I-125-labeled derivative into peptides can be selectively directed towards either alpha- or epsilon-amine functions by modifying the pH of the reaction. Acylation of alpha-amino groups is favored at pH 6.5 whereas epsilon-amino groups react more readily at pH 8.5. We have taken advantage of this result to prepare two new I-125-labeled analogues of substance P and neurotensin that bind selectively and reversibly to their respective receptors. The method described here is of general interest and can be used to incorporate various reporter groups into peptide structures.